Heterocyclic compound and organic light-emitting device including the same

ABSTRACT

A heterocyclic compound represented by Formula 1 below and an organic light-emitting device including the heterocyclic compound: 
     
       
         
         
             
             
         
       
         
         
           
             wherein X 1  and X 2 , X 1  and R 1  to R 10  are defined as in the specification.

CLAIM OF PRIORITY

This application claims the benefit of Korean Patent Application No.10-2011-0114115, filed on 3 Nov. 2011 in the Korean IntellectualProperty Office, the disclosure of which is incorporated herein in itsentirety by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a heterocyclic compound represented byFormula 1 and an organic light-emitting device including theheterocyclic compound.

2. Description of the Related Art

Light-emitting devices are self-emission type display devices and have awide viewing angle, a high contrast ratio, and a short response time.Due to these characteristics, light-emitting devices are drawing moreattention. Such light-emitting devices can be roughly classified intoinorganic light-emitting devices that include emission layers containinginorganic compounds, and organic light-emitting devices that includeemission layers containing organic compounds. Specifically, organiclight-emitting devices have higher luminance, lower driving voltages,and shorter response times than inorganic light-emitting devices, andcan render multi-colored displays. Thus, much research into such organiclight-emitting devices has been conducted. Typically, an organiclight-emitting device has a stack structure including an anode, acathode and an organic emission layer interposed therebetween. However,a hole injection layer and/or a hole transport layer may be furtherstacked between the anode and the organic emission layer, and/or anelectron transport layer may be further stacked between the organicemission layer and the cathode. In other words, an organiclight-emitting device may have a stack structure of anode/hole transportlayer/organic emission layer/cathode or a stack structure of anode/holetransport layer/organic emission layer/electron transport layer/cathode.

As a material for forming the organic emission layer, naphthalenederivatives can be used. However, organic light-emitting devicesincluding such materials may not have satisfactory life span,efficiency, and power consumption characteristics, thereby improvementin this regard still being necessary.

SUMMARY OF THE INVENTION

The present invention provides a novel heterocyclic compound havingimproved electrical characteristics, charge transporting capabilitiesand light-emission capabilities.

The present invention provides an organic light-emitting deviceincluding the heterocyclic compound.

The present invention provides a flat panel display device including theorganic light-emitting device.

According to an aspect of the present invention, there is provided acompound represented by Formula 1 below:

wherein, in Formula 1, R₁ to R₁₀ are each independently a hydrogen atom,a deuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted alkenylgroup, a substituted or unsubstituted C₅-C₆₀ aryl group, an amino groupsubstituted with a substituted or unsubstituted C₅-C₆₀ aryl group, asubstituted or unsubstituted C₃-C₆₀ heteroaryl group, or a substitutedor unsubstituted C₆-C₆₀ condensed polycyclic group;

X₁ and X₂ are each independently —N(R₂₀)— or —S—;

adjacent substituents among R₁ to R₅ or those among R₆ to R₁₀ areoptionally linked to form a ring; and

R₂₀ is a hydrogen atom, a deuterium atom, a halogen group, a cyanogroup, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₁-C₅₀ alkenyl group, a substituted or unsubstitutedC₅-C₆₀ aryl group, an amino group substituted with a substituted orunsubstituted C₅-C₆₀ aryl group, a substituted or unsubstituted C₃-C₆₀heteroaryl group, or a substituted or unsubstituted C₆-C₆₀ condensedpolycyclic group.

In Formula 1, R₁ to R₁₀ and R₂₀ may be each independently a hydrogenatom, a deuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted alkenylgroup, a substituted or unsubstituted C₅-C₃₀ aryl group, an amino groupsubstituted with a substituted or unsubstituted C₅-C₃₀ aryl group, asubstituted or unsubstituted C₅-C₃₀ heteroaryl group, or a substitutedor unsubstituted C₆-C₃₀ condensed polycyclic group.

In Formula 1, R₁ to R₁₀ and R₂₀ may be each independently selected fromthe group consisting of a hydrogen atom, a deuterium atom, a halogenatom, a cyano group, a substituted or unsubstituted C₁-C₂₀ alkyl group,a substituted or unsubstituted C₁-C₂₀ alkenyl group, and groupsrepresented by Formulae 2a to 2j below:

wherein, in Formulae 2a to 2j, Q₁ may be represented by —C(R₃₀)(R₃₁)—,—N(R₃₂)—, —N(-*)-, —S—, or —O—;

Y₁, Y₂, and Y₃ may be each independently represented by —N═, —N(-*)-,—S—, —O—, —C(R₃₃)═, or —C(-*)=.

Z₁, Z₂, Ar₁₂, Ar₁₃, R₃₀, R₃₁, R₃₂, and R₃₃ may be each independentlyselected from the group consisting of a lone pair electron, a hydrogenatom, a deuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted C₅-C₂₀aryl group, a substituted or unsubstituted C₃-C₂₀ heteroaryl group, asubstituted or unsubstituted C₆-C₂₀ condensed polycyclic group, a nitrogroup, a hydroxyl group, and a carboxy group;

Ar₁₁ may be selected from the group consisting of a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₅-C₂₀ arylene group, and a substituted or unsubstituted C₃-C₂₀heteroarylene group;

p may be an integer from 1 to 10;

r may be an integer from 0 to 5; and

* indicates a binding site.

In Formula 1, R₁ to R₁₀ and R₂₀ may be each independently selected fromthe group consisting of a hydrogen atom, a deuterium atom, a halogengroup, a cyano group, a substituted or unsubstituted C₁-C₂₀ alkyl group,a substituted or unsubstituted alkenyl group, and groups represented byFormulae 3a to 3h below:

wherein, in Formulae 3a to 3h, Y₁ may be represented by —N═, —S—, —O—,or —C(R₃₄)—;

Z₁ and Z₂ may be each independently selected from the group consistingof a hydrogen atom, a deuterium atom, a halogen group, a cyano group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₅-C₂₀ aryl group, a substituted or unsubstituted C₃-C₂₀heteroaryl group, a substituted or unsubstituted C₆-C₂₀ condensedpolycyclic group, a nitro group, a hydroxyl group, and a carboxy group;

p and q may be each independently an integer from 1 to 7; and

* indicates a binding site.

The compound represented by Formula 1 may be symmetrical.

In Formula 1, R₁ to R₁₀ and R₂₀ may be each independently selected fromthe group consisting of a hydrogen atom, a deuterium atom, a halogengroup, a cyano group, a substituted or unsubstituted C₁-C₂₀ alkyl group,a substituted or unsubstituted C₁-C₂₀ alkenyl group, and groupsrepresented by Formulae 2a to 2j below; and

the compound represented by Formula 1 may be symmetrical:

wherein, in Formulae 2a to 2j, Q₁ may be represented by —C(R₃₀)(R₃₁)—,—N(R₃₂)—, —N(-*)-, —S—, or —O—;

Y₁, Y₂, and Y₃ may be each independently represented by —N═, —N(-*)-,—S—, —O—, —C(R₃₃)═, or —C(-*)=;

Z₁, Z₂, Ar₁₂, Ar₁₃, R₃₀, R₃₁, R₃₂, and R₃₃ may be each independentlyselected from the group consisting of a lone pair electron, a hydrogenatom, a deuterium atom, a substituted or unsubstituted C₁-C₂₀ alkylgroup, a substituted or unsubstituted C₅-C₂₀ aryl group, a substitutedor unsubstituted C₃-C₂₀ heteroaryl group, a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group, a halogen atom, a cyano group, anitro group, a hydroxyl group, and a carboxy group;

Ar₁₁ may be selected from the group consisting of a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₅-C₂₀ arylene group, and a substituted or unsubstituted heteroarylenegroup;

p may be an integer from 1 to 10;

r may be an integer from 0 to 5; and

* indicates a binding site.

The compound of Formula 1 may be one of the compounds below:

According to another aspect of the present invention, there is providedan organic light-emitting device including: a first electrode; a secondelectrode; and an organic layer between the first electrode and thesecond electrode, wherein the organic layer includes a first layerincluding the compound of Formula 1 above.

The first layer may include at least one layer selected from the groupconsisting of a hole injection layer, a hole transport layer, afunctional layer having both hole injection and hole transportcapabilities, an electron injection layer, an electron transport layer,and a functional layer having both electron injection and electrontransport capabilities.

The organic layer may be an emission layer comprising the compound ofFormula 1 as a host for a fluorescence or phosphorescence device.

The organic layer may include an emission layer, a hole transport layer,and an electron transport layer; and the first layer may be an emissionlayer that further includes an anthracene compound, an arylaminecompound, or a styryl compound.

The organic layer may include an emission layer, a hole transport layer,and an electron transport layer; and the first layer may be an emissionlayer of which a red layer, a green layer, a blue layer, or a whitelayer further includes a phosphorescent compound.

The first layer may be a blue emission layer.

The first layer may be a blue emission layer, and the compound ofFormula 1 may be used as a blue host.

The organic layer may further include a hole injection layer, a holetransport layer, a functional layer having both hole injection and holetransport capabilities, an emission layer, a hole blocking layer, anelectron transport layer, an electron injection layer, or a combinationof at least two thereof.

At least one of the hole injection layer, the hole transport layer, andthe functional layer having hole injection and hole transportcapabilities may further include a charge generating material.

The electron transport layer may include an electron transportingorganic material and a metal-containing material.

The metal-containing material may include a lithium (Li) complex.

The first layer may be formed from the compound of Formula 1 of claim 1using a wet process.

According to another aspect of the present invention, there is provideda flat panel display device including the organic light-emitting devicedescribed above, wherein the first electrode of the organiclight-emitting device is electrically connected to a source electrode ora drain electrode of a thin-film transistor.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other features and advantages of the present inventionwill become more apparent by describing in detail exemplary embodimentsthereof with reference to the attached drawing in which:

FIG. 1 illustrates the structure of an organic light-emitting deviceaccording to an embodiment of the present invention; and

FIG. 2 illustrates a method of making an organic light-emitting deviceof the present invention.

DETAILED DESCRIPTION OF THE INVENTION

As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of,” when preceding a list of elements, modify the entire listof elements and do not modify the individual elements of the list.

Anthracene derivatives are widely known as materials for an organicemission layer. Alq3, PBD, PF-6P, PyPySPyPy, and the like are known aselectron transport materials. For example, an organic light-emittingdevice manufactured using a compound of phenylanthracene dimer or trimeris widely known. However, such organic light-emitting devices have anarrow energy gap and lower blue-light color purity since two or threeoligomeric species of anthracene are linked by conjugation.

In addition, such compounds are highly vulnerable to oxidation and thusare liable to produce impurities, necessitating purification. In orderto overcome these drawbacks, organic light-emitting devices manufacturedusing an anthracene compound including naphthalene substituted foranthracene at 1,9 positions or using a diphenylanthracene compoundincluding an aryl group substituted for a phenyl group at m-positionhave been introduced. However, these organic light-emitting devices havea lower light-emission efficiency.

Organic light-emitting devices may also be manufactured usingnathphalene-substituted monoanthracene derivatives. However, thelight-emission efficiency thereof is low at about 1 cd/A, and thus suchorganic light-emitting devices are not suitable for practical use.Furthermore, organic light-emitting devices may be manufactured usingphenylanthracene compounds including aryl substituents at m-position.Such a compound has excellent thermal resistance but leads to anunsatisfactorily low light-emission efficiency of about 2 cd/A.

The present invention will now be described more fully with reference tothe accompanying drawings, in which exemplary embodiments of theinvention are shown.

An aspect of the present invention provides a heterocyclic compoundrepresented by Formula 1 below.

In Formula 1 above, R₁ to R₁₀ may be each independently a hydrogen atom,a deuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₁-C₅₀alkenyl group, a substituted or unsubstituted C₅-C₆₀ aryl group, anamino group substituted with a substituted or unsubstituted C₅-C₆₀ arylgroup, a substituted or unsubstituted C₃-C₆₀ heteroaryl group, or asubstituted or unsubstituted C₆-C₆₀ condensed polycyclic group: and X₁and X₂ may be each independently —N(R₂₀)— or —S—.

Optionally, adjacent substituents among R₁ to R₅ or those among R₆ toR₁₀ may be linked to form a ring.

R₂₀ is a hydrogen atom, a deuterium atom, a halogen group, a cyanogroup, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₁-C₅₀ alkenyl group, a substituted or unsubstitutedC₅-C₆₀ aryl group, an amino group substituted with a substituted orunsubstituted C₅-C₆₀ aryl group, a substituted or unsubstituted C₃-C₆₀heteroaryl group, or a substituted or unsubstituted C₆-C₆₀ condensedpolycyclic group.

In some embodiments the heterocyclic compound of Formula 1 may be usedas a light-emitting material, an electron-transporting material or anelectron-injecting material.

An organic light-emitting device manufactured using the heterocycliccompound of Formula 1 above may have high durability when stored oroperated.

Substituents in the heterocyclic compound of Formula 1 will now bedescribed in detail.

In some embodiments, in Formula 1, R₁ to R₁₀ and R₂₀ may be eachindependently a hydrogen atom, a deuterium atom, a halogen group, acyano group, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₁-C₂₀ alkenyl group, a substituted orunsubstituted C₅-C₃₀ aryl group, an amino group substituted with asubstituted or unsubstituted C₅-C₃₀ aryl group, a substituted orunsubstituted C₅-C₃₀ heteroaryl group, or a substituted or unsubstitutedC₆-C₃₀ condensed polycyclic group.

In some embodiments, in Formula 1, R₁ to R₁₀ and R₂₀ may be eachindependently selected from the group consisting of a hydrogen atom, adeuterium atom, a halogen atom, a cyano group, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted C₁-C₂₀alkenyl group, and groups represented by Formulae 2a to 2j below:

In Formulae 2a to 2j, Q₁ may be represented by —C(R₃₀)(R₃₁)—, —N(R₃₂)—,—N(-*)-, —S—, or —O—; Y₁, Y₂, and Y₃ may be each independentlyrepresented by —N═, —N(-*)-, —S—, —O—, —C(R₃₃)═, or —C(-*)=;

Z₁, Z₂, Ar₁₂, Ar₁₃, R₃₀, R₃₁, R₃₂, and R₃₃ may be each independentlyselected from the group consisting of a lone pair electron, a hydrogenatom, a deuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted C₅-C₂₀aryl group, a substituted or unsubstituted C₃-C₂₀ heteroaryl group, asubstituted or unsubstituted C₆-C₂₀ condensed polycyclic group, a nitrogroup, a hydroxyl group, and a carboxy group;

Ar₁₁ may be selected from the group consisting of a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₅-C₂₀ arylene group, and a substituted or unsubstituted C₃-C₂₀heteroarylene group:

p may be an integer from 1 to 10; r is an integer from 0 to 5; and *indicates a binding site.

In some embodiments, in Formula 1, R₁ to R₁₀ and R₂₀ may be eachindependently selected from the group consisting of a hydrogen atom, adeuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted C₁-C₂₀alkenyl group, and groups represented by Formulae 3a to 3h below:

In Formulae 3a to 3h, Y₁ may be represented by —N═, —S—, —O—, or—C(R₃₄)═;

Z₁ and Z₂ may be each independently selected from the group consistingof a hydrogen atom, a deuterium atom, a halogen group, a cyano group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₅-C₂₀ aryl group, a substituted or unsubstituted C₃-C₂₀heteroaryl group, a substituted or unsubstituted C₆-C₂₀ condensedpolycyclic group, a nitro group, a hydroxyl group, and a carboxy group;

p and q may be each independently an integer from 1 to 7; and

* indicates a binding site.

In an embodiment of the present invention, the heterocyclic compound ofFormula 1 may be symmetrical. The term “symmetrical” generally meansthat the compound has one or more planes of symmetry.

In some embodiments, in Formula 1, R₁ to R₁₀ and R₂₀ may be eachindependently selected from the group consisting of a hydrogen atom, adeuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted C₁-C₂₀alkenyl group, and groups represented by Formulae 2a to 2j below and theheterocyclic compound of the Formula 1 may be symmetrical.

In Formulae 2a to 2j, Q₁ may be represented by —C(R₃₀)(R₃₁)—, —N(R₃₂)—,—S—, or —O—;

Y₁, Y₂, and Y₃ may be each independently represented by —N═, —N(-*)-,—S—, —O—, —C(R₃₃)═, or —C(-*)=;

Z₁, Z₂, Ar₁₂, Ar₁₃, R₃₀, R₃₁, R₃₂, and R₃₃ may be each independentlyselected from the group consisting of a lone pair electron, a hydrogenatom, a deuterium atom, a substituted or unsubstituted C₁-C₂₀ alkylgroup, a substituted or unsubstituted C₅-C₂₀ aryl group, a substitutedor unsubstituted C₃-C₂₀ heteroaryl group, a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group, a halogen atom, a cyano group, anitro group, a hydroxyl group, and a carboxy group;

Ar₁₁ may be selected from the group consisting of a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₅-C₂₀ arylene group, and a substituted or unsubstituted C₃-C₂₀heteroarylene group:

p may be an integer from 1 to 10;

r may be an integer from 0 to 5; and

* indicates a binding site.

Hereinafter, substituents described with reference to the above formulaewill now be described in detail. In this regard, the numbers of carbonsin substituents are presented only for illustrative purposes and do notlimit the characteristics of the substituents.

The unsubstituted C₁-C₆₀ alkyl group used herein may be linear orbranched. Examples of the alkyl group include, but are not limited to, amethyl group, an ethyl group, a propyl group, an isobutyl group, asec-butyl group, a pentyl group, an iso-amyl group, a hexyl group, aheptyl group, an octyl group, a nonanyl group, and a dodecyl group. Atleast one hydrogen atom of the alkyl group may be substituted with heavyhydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyanogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a C₂-C₁₀ alkenyl group, a C₂-C₁₀ alkynylgroup, a C₆-C₁₆ aryl group, or a C₄-C₁₆ heteroaryl group.

The unsubstituted C₂-C₆₀ alkenyl group indicates an unsaturated alkylgroups having at least one carbon-carbon double bond in the center or ata terminal of the alkyl group. Examples of the alkenyl group include anethenyl group, a propenyl group, a butenyl group, and the like. At leastone hydrogen atom in the unsubstituted alkenyl group may be substitutedwith a substituent described above in conjunction with the alkyl group.

The unsubstituted C₂-C₆₀ alkynyl group indicates an alkyl group havingat least one carbon-carbon triple bond in the center or at a terminal ofthe alkyl group. Examples of the unsubstituted alkynyl group includeacetylene, propylene, phenylacetylene, naphthylacetylene,isopropylacetylene, t-butylacetylene, diphenylacetylene, and the like.At least one hydrogen atom in the alkynyl group may be substituted witha substituent described above in conjunction with the alkyl group.

The unsubstituted C₃-C₆₀ cycloalkyl group indicates a C₃-C₆₀ cyclicalkyl group wherein at least one hydrogen atom in the cycloalkyl groupmay be substituted with a substituent described above in conduction withthe C₁-C₆₀ alkyl group.

The unsubstituted C₁-C₆₀ alkoxy group indicates a group having astructure of —OA wherein A is an unsubstituted C₁-C₆₀ alkyl group asdescribed above. Nonlimiting examples of the unsubstituted C₁-C₆₀ alkoxygroup include a methoxy group, an ethoxy group, a propoxy group, anisopropyloxy group, a butoxy group, and a pentoxy group. At least onehydrogen atom of the alkoxy group may be substituted with a substituentsuch as those described above in conjunction with the alkyl group.

The unsubstituted C₅-C₆₀ aryl group indicates a carbocyclic aromaticsystem containing at least one ring. At least two rings may be fused toeach other or linked to each other by a single bond. The term ‘aryl’refers to an aromatic system, such as phenyl, naphthyl, or anthracenyl.At least one hydrogen atom in the aryl group may be substituted with asubstituent described above in conjunction with the unsubstituted C₁-C₆₀alkyl group.

Examples of the substituted or unsubstituted C₅-C₆₀ aryl group include,but are not limited to, a phenyl group, a C₁-C₁₀ alkylphenyl group (forexample, ethylphenyl group), a halophenyl group (for example, o-, m-,and p-fluorophenyl group, dichlorophenyl group), a cyanophenyl group,dicyanophenyl group, a trifluoromethoxyphenyl group, a biphenyl group, ahalobiphenyl group, a cyanobiphenyl group, a C₁-C₁₀ alkyl biphenylgroup, a C₁-C₁₀ alkoxybiphenyl group, a o-, m-, and p-toryl group, ano-, m-, and p-cumenyl group, a mesityl group, a phenoxyphenyl group, a(α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a(N,N′-diphenyl)aminophenyl group, a pentalenyl group, an indenyl group,a naphthyl group, a halonaphthyl group (for example, fluoronaphthylgroup), a C₁-C₁₀ alkylnaphthyl group (for example, methylnaphthylgroup), a C₁-C₁₀ alkoxynaphthyl group (for example, methoxynaphthylgroup), a cyanonaphthyl group, an anthracenyl group, an azulenyl group,a heptalenyl group, an acenaphthylenyl group, a phenalenyl group, afluorenyl group, an anthraquinolyl group, a methylanthryl group, aphenanthryl group, a triphenylene group, a pyrenyl group, a chrycenylgroup, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, achloroperylenyl group, a pentaphenyl group, a pentacenyl group, atetraphenylenyl group, a hexaphenyl group, a hexacenyl group, arubicenyl group, a coronelyl group, a trinaphthylenyl group, aheptaphenyl group, a heptacenyl group, a pyranthrenyl group, and anovalenyl group.

The unsubstituted C₃-C₆₀ heteroaryl group used herein includes one, twoor three hetero atoms selected from N, O, P and S. At least two ringsmay be fused to each other or linked to each other by a single bond.Examples of the unsubstituted C₄-C₆₀ heteroaryl group include apyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl,group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, apyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinylgroup, a carbazol group, an indol group, a quinolyl group, anisoquinolyl group, and a dibenzothiophene group. In addition, at leastone hydrogen atom in the heteroaryl group may be substituted with asubstituent described above in conjunction with the unsubstituted C₁-C₆₀alkyl group.

The unsubstituted C₅-C₆₀ aryloxy group is a group represented by —OA₁wherein A₁ may be a C₅-C₆₀ aryl group. An example of the aryloxy groupis a phenoxy group. At least one hydrogen atom in the aryloxy group maybe substituted with a substituent described above in conjunction withthe unsubstituted C₁-C₆₀ alkyl group.

The unsubstituted C₅-C₆₀ arylthio group is represented by —SA₁, whereinA₁ may be a C₅-C₆₀ aryl group. Nonlimiting examples of the arylthiogroup include a benzenethio group and a naphthylthio group. At least onehydrogen atom in the arylthio group may be substituted with asubstituent described above in conjunction with the unsubstituted C₁-C₆₀alkyl group.

The unsubstituted C₆-C₆₀ condensed polycyclic group used herein refersto a substituent including at least two rings wherein at least onearomatic ring and/or at least one non-aromatic ring are fused to eachother, and is distinct from an aryl group or a heteroaryl group in termsof being non-aromatic.

Examples of the heterocyclic compound represented by Formula 1 areCompounds 1 to 126 represented by the following formulae. However, theheterocyclic compound of Formula 1 is not be limited to those compounds.

The followings are representative synthetic routes of the heterocycliccompound of Formula 1. Detailed synthetic processes will be describedlater in synthesis examples.

Examples of substituents in the synthetic routes are represented by thefollowing formulae.

Another aspect of the present invention provides an organiclight-emitting device including a first electrode, a second electrode,and an organic layer disposed between the first electrode and the secondelectrode, wherein the organic layer may include a first layercontaining the heterocyclic compound of Formula 1 described above.

The first layer may be at least one layer selected from the groupconsisting of a hole injection layer, a hole transport layer, afunctional layer having both hole injection and hole transportcapabilities, an electron injection layer, an electron transport layer,and a functional layer having both electron injection and electrontransport capabilities.

The first layer may be an emission layer, and the heterocyclic compoundFormula 1 may be used as a host or dopant for a fluorescence orphosphorescence device.

In some embodiments the organic layer of the organic light-emittingdevice may include an emission layer, a hole transport layer and anelectron transport layer. The first layer may be an emission layer thatfurther includes a common anthracene compound, arylamine compound, orstyryl compound.

In addition, at least one hydrogen atom in the anthracene, arylamine orstyryl compound may be substituted with a substituent described above inconjunction with the unsubstituted C₁-C₆₀ alkyl group. The arylaminerefers to a C₅-C₆₀ arylamine group.

In some embodiments the organic layer of the organic light-emittingdevice may include an emission layer, a hole transport layer, and anelectron transport layer, and the first layer may be an emission layerof which one of a red emission layer, a green emission layer, a blueemission layer, and a white emission layer may further include awidely-known phosphorescent compound.

In an embodiment the organic layer of the organic light-emitting devicemay be a blue emission layer. When the first layer of the organiclight-emitting device is a blue emission layer, the heterocycliccompound of Formula 1 may be used as a blue host.

The first electrode may be an anode, and the second electrode may be acathode, but the reverse is also possible.

In some embodiments, the organic light-emitting device may have a firstelectrode/hole injection layer/emission layer/second electrodestructure, a first electrode/hole injection layer/hole transportlayer/emission layer/electron transport layer/second electrodestructure, or a first electrode/hole injection layer/hole transportlayer/emission layer/electron transport layer/electron injectionlayer/second electrode structure. In some other embodiments, the organiclight-emitting device may have a first electrode/single layer havingboth hole injection and hole transport capabilities/emissionlayer/electron transport layer/second electrode structure, or a firstelectrode/single layer having both hole injection and hole transportcapabilities/emission layer/electron transport layer/electron injectionlayer/second electrode structure. In still some other embodiments, theorganic light-emitting device may have a first electrode/hole transportlayer/emission layer/single layer having both electron injection andelectron transport capabilities/second electrode structure, a firstelectrode/hole injection layer/emission layer/single layer having bothelectron injection and electron transport capabilities/second electrodestructure, or a first electrode/hole injection layer/hole transportlayer/emission layer/single layer having both electron injection andelectron transport capabilities/second electrode structure.

In some embodiments of the present invention, the organic light-emittingdevice may have any of a variety of structures, for example, may beeither a top-emission organic light-emitting device or a bottom-emissionorganic light-emitting device.

In some embodiments, the organic layer of the organic light-emittingdevice may further include, but are not limited to, a hole injectionlayer, a hole transport layer, a functional layer having both holeinjection and hole transport capabilities, an emission layer, a holeblocking layer, an electron transport layer, an electron injectionlayer, or a combination of at least two thereof. At least one of thehole injection layer, the hole transport layer, and the functional layerhaving both hole injection and hole transport capabilities may furtherinclude a charge generating material for improved layer conductivity, inaddition to the heterocyclic compound of Formula 1 described above, awidely-known hole injection material, and a widely-known hole transportmaterial.

The charge generating material may be, for example, a p-dopant.Non-limiting examples of the p-dopant are quinone derivatives such astetracyanoquinonedimethane (TCNQ),2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4TCNQ), andthe like; metal oxides such as tungsten oxide, molybdenum oxide, and thelike; and cyano-containing compounds such as Compound 100 below.

When the hole injection layer, the hole transport layer, or thefunctional layer having both hole injection and hole transportcapabilities further includes a charge generating material, the chargegenerating material may be, but not limited to, homogeneously dispersedor inhomogeneously distributed in the layer.

In some embodiments the electron transport layer of the organiclight-emitting device may further include an electron-transportingorganic compound and a metal-containing material. Non-limiting examplesof the electron-transporting organic compound include9,10-di(naphthalen-2-yl)anthracene (ADN), and anthracene-basedcompounds, such as Compounds 101 and 102 below.

The metal-containing material may include a lithium (Li) complex.Non-limiting examples of the Li complex include lithium quinolate (LiQ)and Compound 103 below:

Hereinafter, a method of manufacturing an organic light-emitting deviceaccording to an embodiment of the present invention will be describedwith reference to FIG. 1. FIG. 1 illustrates the structure of an organiclight-emitting device according to an embodiment of the presentinvention. FIG. 2 shows a method of manufacturing an organiclight-emitting device according to an embodiment of the presentinvention. Referring to FIG. 1, the organic light-emitting deviceaccording to the present embodiment includes a substrate (not shown), afirst electrode (anode), a hole injection layer (HIL), a hole transportlayer (HTL), an emission layer (EML), an electron transport layer (ETL),an electron injection layer (EIL), and a second electrode (cathode).

First, a first electrode is formed on a substrate by using a depositionor sputtering method. The first electrode may be formed from a firstelectrode material having a high work function. The first electrode mayconstitute an anode or a cathode. The substrate may be a substrateconventionally used in organic light-emitting devices, and may be, forexample, a glass substrate or a transparent plastic substrate withstrong mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water resistance. Examples of thefirst electrode material are materials, such as indium tin oxide (ITO),indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), aluminum(Al), silver (Ag), and magnesium (Mg), which have high conductivity. Thefirst electrode may be formed as a transparent or reflective electrode.

Next, the HIL may be formed on the first electrode using variousmethods, for example, by vacuum deposition, spin coating, casting,Langmuir-Blodgett (LB) deposition, or the like.

When the HIL is formed using vacuum deposition, the depositionconditions may vary according to the material that is used to form theHIL, and the structure and thermal characteristics of the HIL. Forexample, the deposition conditions may include a deposition temperatureof about 100 to about 500° C., a vacuum pressure of about 10⁻⁸ to about10⁻³ torr, and a deposition rate of about 0.01 to about 100 Å/sec.

When the HIL is formed using spin coating, coating conditions may varyaccording to the material used to form the HIL, and the structure andthermal properties of the HIL. For example, the coating conditions mayinclude a coating speed of about 2000 rpm to about 5000 rpm, and athermal treatment temperature of about 80° C. to about 200° C. at whichthe solvent remaining after coating may be removed.

The HIL may be formed of any material that is commonly used to form aHIL. Examples of the material that can be used to form the HIL are aphthalocyanine compound such as copperphthalocyanine,4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA),N,N′-di(1-naphthyl)-N,N′-diphenylberrzidine (NPB), TDATA, 2T-NATA,polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOTIPSS),polyaniline/camphor sulfonic acid (Pani/CSA), andpolyaniline)/poly(4-styrenesulfonate (PANI/PSS), but are not limitedthereto.

The HIL may have a thickness of about 100 Å to about 10000 Å, and insome other embodiments, may have a thickness of about 100 Å to about1000 Å. When the thickness of the HIL is within these ranges, the HILmay have good hole injection characteristics without an increase indriving voltage.

Next, the HTL may be formed on the HIL using any of a variety ofmethods, for example, vacuum deposition, spin coating, casting, LBdeposition, or the like. When the HTL is formed using vacuum depositionor spin coating, the deposition or coating conditions may be similar tothose applied to form the HIL, though the deposition or coatingconditions may vary according to the material that is used to form theHTL.

The HTL may be formed of the heterocyclic compound of Formula 1 above orany known HTL material. Non-limiting examples of such HTL materialsinclude carbazole derivatives such as N-phenylcarbazole orpolyvinylcarbazole, and amine derivatives having an aromatic condensedring, such as NPB,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), or the like.

The HTL may have a thickness of about 50 Å to about 1000 Å, and in someembodiments, may have a thickness of about 100 Å to about 600 Å. Whenthe thickness of the HTL is within these ranges, the HTL may have goodhole transport characteristics without a substantial increase in drivingvoltage.

Next, the EML may be formed on the HTL using any of a variety ofmethods, for example, by vacuum deposition, spin coating, casting, LBdeposition, or the like. When the EML is formed using vacuum depositionor spin coating, the deposition or coating conditions may be similar tothose applied to form the HIL, though the deposition or coatingconditions may vary according to the material that is used to form theEML.

The EML may include the heterocyclic compound of Formula 1 describedabove. For example, the heterocyclic compound of Formula 1 may be usedas a host or a dopant. The EML may be formed using any of a variety ofwell-known light-emitting materials, in addition to the heterocycliccompound of Formula 1. In some embodiments the EML may also be formedusing a well-known host and a dopant. Dopants that may be used to formthe EML may be either a fluorescent dopant or a phosphorescent dopantwhich are widely known in the art.

Non-limiting examples of the host are Alq3,4,4′-N,N′-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK),9,10-di(naphthalene-2-yl)anthracene (ADN), TCTA,1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI),3-cert-butyl-9,10-di-2-naphthylanthracene (TBADN), E3, anddistyrylarylene (DSA).

Examples of red dopants include, but are not limited to, platinum(II)oclaethylporphyrin (PtOEP), Ir(piq)₃, Btp₂Ir(acac), and DCJTB.

Examples of green dopants may include, but are not limited to, Ir(ppy)₃(where “ppy” denotes phenylpyridine), Ir(ppy)₂(acac), Ir(mpyp)₃, andC545T.

Examples of blue dopants include F₂Irpic, (F₂ppy)₂Ir(tmd), Ir(dfppz)₃,ter-fluorene, 4,4′-bis(4-diphenylaminostyryl)biphenyl (DPAVB1), and2,5,8,11-tetra-t-butyl phenylene (TBP), but are not limited thereto.

The amount of the dopant may be from about 0.1 to about 20 parts byweight, and in some other embodiments, may be from about 0.5 to about 12parts by weight, based on 100 parts by weight of the EML material(equivalent to the total weight of the host and dopant). When the amountof the dopant is within these ranges, concentration quenching may besubstantially prevented.

The EML may have a thickness of about 100 Å to about 1,000 Å, and insome embodiments, may have a thickness of about 200 Å to about 600 Å.When the thickness of the EML is within these ranges, the EML may havegood light-emitting characteristics without a substantial increase indriving voltage.

When the EML includes a phosphorescent dopant, a hole blocking layer(HBL, not shown in FIG. 1) may be formed on the EML in order to preventdiffusion of triplet excitons or holes into the ETL. In this case, theHBL may be formed from any material commonly used to form a HBL.Examples of such HBL materials are, but are not limited to, oxadiazolederivatives, triazole derivatives, phenathroline derivatives, Balq, andBCP.

The HBL may have a thickness of about 50 Å to about 1,000 Å, and in someembodiments, may have a thickness of about 100 Å to about 300 Å. Whenthe thickness of the HBL is within these ranges, diffusion of tripletexitons or holes into the ETL may be readily prevented without asubstantial increase in driving voltage. Next, the ETL is formed on theEML (or HBL) using various methods, for example, by vacuum deposition,spin coating, casting, or the like. When the ETL is formed using vacuumdeposition or spin coating, the deposition or coating conditions may besimilar to those applied to form the HIL, though the deposition orcoating conditions may vary according to the material that is used toform the ETL.

The ETL material may be the heterocyclic compound of Formula 1 describedabove, and in some embodiments, may be any arbitrary material selectedfrom among electron transporting materials widely known in the art.Examples of the ETL material include, but are not limited to, quinolinederivatives, such as tris(8-quinolinolate)aluminum (Alq3), TAZ, andBAlq.

The ETL may have a thickness of about 100 Å to about 1,000 Å, and insome other embodiments, may have a thickness of about 100 Å to about 500Å. When the thickness of the ETL is within these ranges, the ETL mayhave good electron transport characteristics without a substantialincrease in driving voltage.

In addition, the EIL, which facilitates injection of electrons from thecathode, may be formed on the ETL.

The EIL may be formed using any known materials used to form an EILlayer, for example, LiF, NaCl, CsF, Li₂O, BaO, or the like. Thedeposition or coating conditions may be similar to those applied to formthe HIL, although the deposition and coating conditions may varyaccording to the material that is used to form the EIL.

The EIL may have a thickness of about 1 Å to 100 Å, and in someembodiments, may have a thickness of about 5 Å to about 90 Å. When thethickness of the EIL is within these ranges, the EIL may have goodelectron injection characteristics without a substantial increase indriving voltage.

Finally, the second electrode may be formed on the EIL by using, forexample, vacuum deposition, sputtering, or the like. The secondelectrode may constitute a cathode or an anode. The material for formingthe second electrode may be a metal, an alloy, or an electricallyconductive compound, which are materials having a low work function, ora mixture thereof. Examples of such materials are, but are not limitedto, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver(Mg—Ag). In addition, in order to manufacture a top-emission organiclight-emitting device, a transparent cathode formed of a transparentmaterial such as ITO or IZO may be used as the second electrode.

According to embodiments of the present invention, the organiclight-emitting device may be included in various types of flat paneldisplay devices, such as in a passive matrix organic light-emittingdisplay device or in an active matrix organic light-emitting displaydevice. In particular, when the organic light-emitting device isincluded in an active matrix organic light-emitting display deviceincluding a thin-film transistor, the first electrode on the substratemay function as a pixel electrode, electrically connected to a sourceelectrode or a drain electrode of the thin-film transistor. Moreover,the organic light-emitting device may also be included in flat paneldisplay devices having double-sided screens.

According to embodiments, the organic light-emitting device may includea plurality of organic layers, wherein at least one of the organiclayers may be formed of the heterocyclic compound of Formula 1 by usinga deposition method or a wet method of coating a solution of theheterocyclic compound of Formula 1.

Hereinafter, synthesis examples of Compounds 1, 14, 24, 70 and 83 andexamples will be described in detail. However, these examples arepresented for illustrative purposes only, and do not limit the scope ofthe present invention.

EXAMPLES Representative Synthetic Routes

Representative Synthesis Example Synthesis of Compound 1

Synthesis of Intermediate 1-a

After 10.0 g (44.83 mmol) of 8-bromo-naphthalene-2-ol was dissolved in100 mL of toluene, 5 g (53.79 mmol) of aniline, 6.5 g (67.24 mmol) ofsodium tert-butoxide and 3.3 g (3.59 mmol) oftris(dibenzylideneacetone)dipalladium(0) were added to the solution andstirred at about 120° C. for about 18 hours. After completion of thereaction, toluene was removed by distillation in a reduced pressure,followed by an addition of 50.0 mL of distilled water and extractionthree times each with 70.0 mL of methylene chloride. The organic phasewas collected, and was dried using magnesium sulfate and the solvent wasevaporated. The residue was separated and purified using silica gelcolumn chromatography to obtain 9.8 g (41.65 mmol) of Intermediate 1-a(Yield: 92.9%). This compound was identified using liquidchromatography-mass spectroscopy (LC-MS). C16H13NO: M+ 236.10

Synthesis of Intermediate 1-b

After 8.0 g (34.00 mmol) of Intermediate 1-a was dissolved in 80 mL ofdichloromethane, 6.1 mL (36.26 mmol) of trifluoromethanesulfonicanhydride and 5.7 mL (40.87 mmol) of triethyl amine were added to thesolution and stirred for about 4 hours. After completion of thereaction, 20.0 mL of distilled water was added to stop the reaction.After extraction three times each with 50.0 mL of methylene chloride,the organic phase was collected and was dried using magnesium sulfateand the solvent was evaporated. The residue was separated and purifiedby silica gel column chromatography to obtain 11.5 g (31.31 mmol) ofIntermediate 1-b (Yield: 92.1%). This compound was identified usingLC-MS. C17H12F3NO3S: M+ 368.05

Synthesis of Intermediate 1-c

After 10.2 mL (20.43 mmol) of lithium diisopropyl amide (LDA, 2MSolution in Et₂O) was diluted with 30.0 mL of diethylether in a flaskfilled with nitrogen, the temperature was lowered to about −78° C. Asolution of 5.0 g (13.62 mmol) of the Intermediate 1-b dissolved in 20.0mL of diethylether was slowly dropwise added into the flask for about 15minutes and stirred for about 1 hour. 3.7 mL (16.35 mmol) oftriisopropylborate was slowly dropwise added to the solution and stirredat room temperature for about 1 hour. After completion of the reaction,50 mL of an aqueous 5% NaOH solution was slowly added thereto. After apH adjustment to about 1-2 by an addition of 80 mL of a 3N HCl solution,and extraction three times each with 50.0 mL of ethylacetate, theorganic phase was collected and was dried using magnesium sulfate andthe solvent was evaporated. The residue was separated and purified bysilica gel column chromatography to obtain 1.5 g (3.65 mmol) ofIntermediate 1-c (Yield: 26.8%). This compound was identified usingLC-MS. C17H13BF3NO5S: M+ 412.07

Synthesis of Intermediate 1-d

4.5 g (12.23 mmol) of the Intermediate 1-b, and 1.8 g (14.67 mmol) ofpotassium bromide (KBr) were added to 40.0 mL of a mixed acid solution(nitric acid:sulfuric acid=1:2) and vigorously stirred at about 100° C.for about 24 hours. After completion of the reaction, 200.0 mL of waterwas added to the mixture, followed by a pH adjustment to about 7 usingan aqueous NaOH solution. The resulting solid was filtrated and washedwith dichloromethane. After extraction three times each with 80.0 mL ofdichloromethane, the organic phase was collected and was dried usingmagnesium sulfate and the solvent was evaporated. The residue wasseparated and purified by silica gel column chromatography to obtain1.23 g (2.76 mmol) of Intermediate 1-d (Yield: 22.5%). This compound wasidentified using LC-MS. C17H11BrF3NO3S: M+ 445.99

Synthesis of Compound 1

2.0 g (4.86 mmol) of the Intermediate 1-c and 1.8 g (4.05 mmol) of theIntermediate 1-d were dissolved in 35.0 mL of tetrahydrofuran (THF).234.2 mg (0.20 mmol) of Pd(PPh3)₄ and 5.0 mL of an aqueous 5% K₂CO₃solution (by weight) were added to the solution and stirred at about120° C. for about 24 hours under reflux. After completion of thereaction, the temperature was cooled to room temperature, and 20.0 mL ofwater was added to stop the reaction. After extraction three times eachwith 70.0 mL of ethylacetate, the organic phase was collected and wasdried using magnesium sulfate and the solvent was evaporated. Theresidue was separated and purified by silica gel column chromatographyto obtain 0.83 g (1.92 mmol) of Compound 1 (Yield: 39.5%). This compoundwas identified using LC-MS. C32H20N2: M+ 433.16

Synthesis Example 2 Synthesis of Compound 14

Synthesis of Intermediate 2-a

10.0 g (54.22 mmol) of cyanuric chloride was dissolved in 35 mL oftetrahydrofuran (THF), and the solution was cooled to 0° C. 45.1 mL(135.56 mmol) of phenyl magnesium bromide (3.0M in diethylether) wasslowly added to the solution and stirred at room temperature for about 3hours. The resulting solid was filtrated in a reduced pressure andwashed with methanol and hexane to obtain 9.0 g of (33.62 mmol) ofIntermediate 2-a (Yield: 62.0%). This compound was identified usingLC-MS. C15H10ClN3: M+ 268.06

Synthesis of Intermediate 2-b

After 10.0 g (62.82 mmol) of 8-amino-2-naphthol was dissolved in 100 mLof toluene, 20.2 g (75.38 mmol) of the Intermediate 2-a, 9.1 g (94.23mmol) of sodium tert-butoxide and 4.6 g (5.03 mmol) oftris(dibenzylideneacetone)dipalladium(0) were added to the solution andstirred at about 120° C. for about 18 hours. After completion of thereaction, toluene was removed by distillation in a reduced pressure,followed by an addition of 50.0 mL of distilled water and extractionthree times each with 70.0 mL of methylene chloride. The organic phasewas collected, and was dried using magnesium sulfate and the solvent wasevaporated. The residue was separated and purified using silica gelcolumn chromatography to obtain 24.8 g (57.1 mmol) of Intermediate 2-b(Yield: 90.9%). This compound was identified using LC-MS. C25H18N40: M+390.15

Synthesis of Intermediate 2-c

After 12.0 g (27.62 mmol) of Intermediate 2-b was dissolved in 80 mL ofdichloromethane, 5.4 mL (32.27 mmol) of trifluoromethanesulfonicanhydride and 5.1 mL (36.88 mmol) of triethyl amine were added to thesolution and stirred for about 4 hours. After completion of thereaction, 20.0 mL of distilled water was added to stop the reaction.After extraction three times each with 50.0 mL of methylene chloride,the organic phase was collected and was dried using magnesium sulfateand the solvent was evaporated. The residue was separated and purifiedby silica gel column chromatography to obtain 14.2 g (27.18 mmol) ofIntermediate 2-c (Yield: 88.4%). This compound was identified usingLC-MS. C26H17F3N4O3S: M+ 523.10

Synthesis of Intermediate 2-d

After 5.02 mL (10.1 mmol) of lithium diisopropyl amide (LDA, 2M solutionin Et₂O) was diluted with 30.0 mL of diethylether in a flask filled withnitrogen, the temperature was lowered to about −78° C. A solution of3.50 g (6.7 mmol) of the Intermediate 2-c dissolved in 20.0 mL ofdiethylether was slowly dropwise added into the flask for about 15minutes and stirred for about 1 hour. 1.86 mL (8.00 mmol) oftriisopropylborate was slowly dropwise added to the solution and stirredat room temperature for about 1 hour. After completion of the reaction,50 mL of an aqueous 5% NaOH solution was slowly added thereto. After apH adjustment to about 1 to 2 by an addition of 80 mL of a 3N HClsolution, and extraction three times each with 70.0 mL of ethylacetate,the organic phase was collected and was dried using magnesium sulfateand the solvent was evaporated. The residue was separated and purifiedby silica gel column chromatography to obtain 1.2 g (2.12 mmol) ofIntermediate 2-d (Yield: 31.6%). This compound was identified usingLC-MS. C26H18BF3N4O5S: M+ 567.10

Synthesis of Intermediate 2-e

4.5 g (8.61 mmol) of the Intermediate 2-c, and 1.8 g (10.33 mmol) ofpotassium bromide (KBr) were added to 40.0 mL of a mixed acid solution(nitric acid:sulfuric acid=1:2) and vigorously stirred at about 100° C.for about 24 hours. After completion of the reaction, 200.0 mL of waterwas added to the mixture, followed by a pH adjustment to about 7 usingan aqueous NaOH solution. The resulting solid was filtrated and washedwith dichloromethane. After extraction three times each with 80.0 mL ofdichloromethane, the organic phase was collected and was dried usingmagnesium sulfate and the solvent was evaporated. The residue wasseparated and purified by silica gel column chromatography to obtain 1.1g (1.75 mmol) of Intermediate 2-e (Yield: 20.3%). This compound wasidentified using LC-MS. C26H16BrF3N4O3S: M+ 601.32

Synthesis of Compound 14

Tdhfjv 1.0 g (1.77 mmol) of the Intermediate 2-d and 0.9 g (1.47 mmol)of the Intermediate 2-e were dissolved in 20.0 mL of tetrahydrofuran(THF). 85.0 mg (0.07 mmol) of Pd(PPh3)₄ and 5.0 mL of an aqueous 5%K₂CO₃ solution (by weight) were added to the solution and stirred atabout 120° C. for about 24 hours under reflux. After completion of thereaction, the temperature was cooled to room temperature, and 30.0 mL ofwater was added to stop the reaction. After extraction three times eachwith 40.0 mL of ethylacetate, the organic phase was collected and wasdried using magnesium sulfate and the solvent was evaporated. Theresidue was separated and purified by silica gel column chromatographyto obtain 0.22 mg (0.51 mmol) of Compound 14 (Yield: 28.8%). Thiscompound was identified using LC-MS. C50H30N8: M+ 743.00

Synthesis Example 3 Synthesis of Compound 24

Synthesis of Intermediate 3-a

After 4.5 g (12.25 mmol) of Intermediate 1-b was dissolved in 50 mL ofchloroform to obtain a solution, a dilution of 0.7 mL (13.48 mmol) ofbromine (Br₂) with 5.0 mL of chloroform was slowly dropwise added to thesolution for about 10 minutes and stirred at room temperature overnight.The solvent was distilled in a reduced pressure, and the residue wasrecrystallized using ethylacetate/hexane. The resulting solid wasfiltrated and dried to obtain 1.1 g (2.35 mmol) of an Intermediate 3-a(Yield: 19.2%). This compound was identified LC-MS. C17H13BF3NO5S: M+445.96

Synthesis of Intermediate 3-b

1.4 g (6.72 mmol) of dibenzofurane boronic acid and 2.0 g (4.48 mmol) ofthe Intermediate 3-a were dissolved in 30.0 mL of tetrahydrofuran (THF).260.2 mg (0.22 mmol) of Pd(PPh3)₄ and 1.9 g (13.45 mmol) of K₂CO₃ wereadded to the solution and stirred at about 120° C. for about 24 hoursunder reflux. After completion of the reaction, the temperature wascooled to room temperature, and 50.0 mL of water was added to stop thereaction. After extraction three times each with 70.0 mL ofethylacetate, the organic phase was collected and was dried usingmagnesium sulfate and the solvent was evaporated. The residue wasseparated and purified by silica gel column chromatography to obtain 1.2g (2.25 mmol) of Intermediate 3-b (Yield: 50.2%). This compound wasidentified using LC-MS. C29H18F3NO4S: M+ 534.09

Synthesis of Intermediate 3-c

After 4.2 mL (8.43 mmol) of lithium diisopropyl amide (LDA, 2M solutionin Et₂O) was diluted with 40.0 mL of diethylether in a flask filled withnitrogen, the temperature was lowered to about −78° C. A solution of 3.0g (5.62 mmol) of the Intermediate 3-b dissolved in 10.0 mL ofdiethylether was slowly dropwise added into the flask for about 15minutes and stirred for about 1 hour. 1.56 mL (6.75 mmol) oftriisopropylborate was slowly dropwise added to the solution and stirredat room temperature for about 1 hour. After completion of the reaction,50 mL of an aqueous 5% NaOH solution was slowly added thereto. After apH adjustment to about 1 to 2 by an addition of 80.0 mL of a 3N HClsolution, and extraction three times each with 50.0 mL of ethylacetate,the organic phase was collected and was dried using magnesium sulfateand the solvent was evaporated. The residue was separated and purifiedby silica gel column chromatography to obtain 1.1 g (1.91 mmol) ofIntermediate 3-c (Yield: 33.9%). This compound was identified usingLC-MS. C29H19BF3NO6S: M+ 578.10

Synthesis of Intermediate 3-d

3.0 g (5.62 mmol) of the Intermediate 3-b, and 1.8 g (6.75 mmol) ofpotassium bromide (KBr) were added to 27.0 mL of a mixed acid solution(nitric acid:sulfuric acid=1:2) and vigorously stirred at about 100° C.for about 24 hours. After completion of the reaction, 250.0 mL of waterwas added to the mixture, followed by a pH adjustment to about 7 usingan aqueous NaOH solution. The resulting solid was filtrated and washedwith dichloromethane. After extraction three times each with 70.0 mL ofdichloromethane, the organic phase was collected and was dried usingmagnesium sulfate and the solvent was evaporated. The residue wasseparated and purified by silica gel column chromatography to obtain 1.1g (1.71 mmol) of Intermediate 3-d (Yield: 30.5%). This compound wasidentified using LC-MS. C29H17BrF3NO4S: M+ 612.00

Synthesis of Compound 24

1.5 g (2.60 mmol) of the Intermediate 3-c and 1.3 g (2.17 mmol) of theIntermediate 3-d were dissolved in 40.0 mL of tetrahydrofuran (THF).125.1 mg (0.11 mmol) of Pd(PPh3)₄ and 8.0 mL of an aqueous 5% K₂CO₃solution (by weight) were added to the solution and stirred at about120° C. for about 24 hours under reflux. After completion of thereaction, the temperature was cooled to room temperature, and 30.0 mL ofwater was added to stop the reaction. After extraction three times eachwith 50.0 mL of ethylacetate, the organic phase was collected and wasdried using magnesium sulfate and the solvent was evaporated. Theresidue was separated and purified by silica gel column chromatographyto obtain 730 mg (0.95 mmol) of Compound 24 (Yield: 36.7%). Thiscompound was identified using liquid LC-MS. C56H32N2O2: M+ 765.25

Synthesis Example 4 Synthesis of Compound 70

Synthesis of Intermediate 4-a

After 8.0 g (45.40 mmol) of 8-mercapto-naphthalene-2-ol was dissolved in80 mL of dichloromethane, 8.0 mL (47.66 mmol) oftrifluoromethanesulfonic anhydride and 7.6 mL (54.47 mmol) of triethylamine were added to the solution and stirred for about 4 hours. Aftercompletion of the reaction, 20.0 mL of distilled water was added to stopthe reaction. After extraction three times each with 60.0 mL ofmethylene chloride, the organic phase was collected and was dried usingmagnesium sulfate and the solvent was evaporated. The residue wasseparated and purified by silica gel column chromatography to obtain12.5 g (40.54 mmol) of Intermediate 4-a (Yield: 89.3%). This compoundwas identified using LC-MS. C11H7F3O3S2: M+ 308.99

Synthesis of Intermediate 4-b

After 8.5 mL (17.03 mmol) of lithium diisopropyl amide (LDA, 2M solutionin Et₂O) was diluted with 35.0 mL of diethylether in a flask filled withnitrogen, the temperature was lowered to about −78° C. A solution of 3.5g (11.35 mmol) of the Intermediate 4-a dissolved in 30.0 mL ofdiethylether was slowly dropwise added into the flask for about 15minutes and stirred for about 1 hour. 3.7 mL (13.62 mmol) oftriisopropylborate was slowly dropwise added to the solution and stirredat room temperature for about 1 hour. After completion of the reaction,80.0 mL of an aqueous 5% NaOH solution was slowly added thereto. After apH adjustment to about 1 to 2 by an addition of 120.0 mL of a 3N HClsolution, and extraction three times each with 80.0 mL of ethylacetate,the organic phase was collected and was dried using magnesium sulfateand the solvent was evaporated. The residue was separated and purifiedby silica gel column chromatography to obtain 1.1 g (3.12 mmol) ofIntermediate 4-b (Yield: 27.5%). This compound was identified usingLC-MS. C11H8BF3O5S2: M+ 352.99

Synthesis of Intermediate 4-c

6.8 g (19.24 mmol) of the Intermediate 4-b and 2.0 g (12.82 mmol) ofbenzene bromide were dissolved in 100.0 mL of tetrahydrofuran (THF). 740mg (0.64 mmol) of Pd(PPh3)₄ and 5.3 g (38.47 mmol) of K₂CO₃ were addedto the solution and stirred at about 120° C. for about 24 hours underreflux. After completion of the reaction, the temperature was cooled toroom temperature, and 80.0 mL of water was added to stop the reaction.After extraction three times each with 100.0 mL of ethylacetate, theorganic phase was collected and was dried using magnesium sulfate andthe solvent was evaporated. The residue was separated and purified bysilica gel column chromatography to obtain 2.8 g (7.28 mmol) ofIntermediate 4-c (Yield: 56.8%). This compound was identified usingLC-MS. C17H11F3O3S2: M+ 385.01

Synthesis of Intermediate 4-d

After 6.8 mL (13.66 mmol) of lithium diisopropyl amide (LDA, 2M solutionin Et₂O) was diluted with 50.0 mL of diethylether in a flask filled withnitrogen, the temperature was lowered to about −78° C. A solution of 3.5g (9.11 mmol) of the Intermediate 4-c dissolved in 25.0 mL ofdiethylether was slowly dropwise added into the flask for about 15minutes and stirred for about 1 hour. 2.5 mL (10.93 mmol) oftriisopropylborate was slowly dropwise added to the solution and stirredat room temperature for about 1 hour. After completion of the reaction,80.0 mL of an aqueous 5% NaOH solution was slowly added thereto. After apH adjustment to about 1 to 2 by an addition of 120.0 mL of a 3N HClsolution, and extraction three times each with 80.0 mL of ethylacetate,the organic phase was collected and was dried using magnesium sulfateand the solvent was evaporated. The residue was separated and purifiedby silica gel column chromatography to obtain 1.5 g (3.48 mmol) ofIntermediate 4-d (Yield: 38.2%). This compound was identified usingLC-MS. C17H12BF3O5S2: M+ 429.01

Synthesis of Intermediate 4-e

3.5 g (9.11 mmol) of the Intermediate 4-c, and 1.3 g (10.93 mmol) ofpotassium bromide (KBr) were added to 32.0 mL of a mixed acid solution(nitric acid:sulfuric acid=1:2) and vigorously stirred at about 100° C.for about 24 hours. After completion of the reaction, 160.0 mL of waterwas added to the mixture, followed by a pH adjustment to about 7 usingan aqueous NaOH solution. The resulting solid was filtrated and washedwith dichloromethane. After extraction three times each with 80.0 mL ofdichloromethane, the organic phase was collected and was dried usingmagnesium sulfate and the solvent was evaporated. The residue wasseparated and purified by silica gel column chromatography to obtain 1.2g (2.59 mmol) of Intermediate 4-e (Yield: 28.5%). This compound wasidentified using LC-MS. C17H10BrF3O3S2: M+ 462.95

Synthesis of Compound 70

1.5 g (3.50 mmol) or the Intermediate 4-d and 1.4 g (2.92 mmol) of theIntermediate 4-e were dissolved in 30.0 mL of tetrahydrofuran (THF).168.7 mg (0.15 mmol) of Pd(PPh3)₄ and 5.0 mL of an aqueous 5% K₂CO₃solution (by weight) were added to the solution and stirred at about120° C. for about 24 hours under reflux. After completion of thereaction, the temperature was cooled to room temperature, and 30.0 mL ofwater was added to stop the reaction. After extraction three times eachwith 80.0 mL of ethylacetate, the organic phase was collected and wasdried using magnesium sulfate and the solvent was evaporated. Theresidue was separated and purified by silica gel column chromatographyto obtain 0.73 g (1.56 mmol) of Compound 70 (Yield: 44.7%). Thiscompound was identified using LC-MS. C32H18S2: M+ 467.05

Synthesis Example 5 Synthesis of Compound 83

Synthesis of Intermediate 5-a

After 5.0 g (16.22 mmol) of Intermediate 4-a was dissolved in 35.0 mL ofchloroform to obtain a solution, a dilution of 0.9 mL (17.84 mmol) ofbromine (Br₂) with 15.0 mL of chloroform was slowly dropwise added tothe solution for about 10 minutes and stirred at room temperatureovernight. The solvent was distilled in a reduced pressure, and theresidue was recrystallized using ethylacetate/hexane. The resultingsolid was filtrated and dried to obtain 1.3 g (3.36 mmol) of anIntermediate 5-a (Yield: 20.1%). This compound was identified usingLC-MS. C11H6BrF3O3S2: M+ 386.85

Synthesis of Intermediate 5-b

4.1 g (19.37 mmol) of dibenzofurane boronic acid and 5.0 g (12.91 mmol)of the Intermediate 5-a were dissolved in 80.0 mL of tetrahydrofuran(THF). 750 mg (0.65 mmol) of Pd(PPh3)₄ and 5.4 g of K₂CO₃ were added tothe solution and stirred at about 120° C. for about 24 hours underreflux. After completion of the reaction, the temperature was cooled toroom temperature, and 30.0 mL of water was added to stop the reaction.After extraction three times each with 80.0 mL of ethylacetate, theorganic phase was collected and was dried using magnesium sulfate andthe solvent was evaporated. The residue was separated and purified bysilica gel column chromatography to obtain 2.8 g (5.90 mmol) ofIntermediate 5-b (Yield: 45.7%). This compound was identified usingLC-MS. C23H13F3O4S2: M+474.47

Synthesis of Intermediate 5-c

After 5.5 mL (11.06 mmol) of lithium diisopropyl amide (LDA, 2M solutionin Et₂O) was diluted with 50.0 mL of diethylether in a flask filled withnitrogen, the temperature was lowered to about −78° C. A solution of 3.5g (7.38 mmol) of the Intermediate 5-b dissolved in 20.0 mL ofdiethylether was slowly dropwise added into the flask for about 15minutes and stirred for about 1 hour. 2.5 mL (8.85 mmol) oftriisopropylborate was slowly dropwise added to the solution and stirredat room temperature for about 1 hour. After completion of the reaction,65.0 mL of an aqueous 5% NaOH solution was slowly added thereto. After apH adjustment to about 1 to 2 by an addition of 89.0 mL of a 3N HClsolution, and extraction three times each with 90.0 mL of ethylacetate,the organic phase was collected and was dried using magnesium sulfateand the solvent was evaporated. The residue was separated and purifiedby silica gel column chromatography to obtain 1.7 g (3.28 mmol) ofIntermediate 5-c (Yield: 44.5%). This compound was identified usingLC-MS. C23H14BF3O6S2: M+ 519.02

Synthesis of Intermediate 5-d

3.5 g (7.38 mmol) of the Intermediate 5-b, and 1.1 g (8.85 mmol) ofpotassium bromide (KBr) were added to 31.5 mL of a mixed acid solution(nitric acid:sulfuric acid=1:2) and vigorously stirred at about 100° C.for about 24 hours. After completion of the reaction, 158.0 mL of waterwas added to the mixture, followed by a pH adjustment to about 7 usingan aqueous NaOH solution. The resulting solid was filtrated and washedwith dichloromethane. After extraction three times each with 70.0 mL ofdichloromethane, the organic phase was collected and was dried usingmagnesium sulfate and the solvent was evaporated. The residue wasseparated and purified by silica gel column chromatography to obtain 1.1g (2.01 mmol) of Intermediate 5-d (Yield: 27.2%). This compound wasidentified using LC-MS. C23H12BrF3O4S2: M+ 552.95

Synthesis of Compound 83

1.5 g (2.89 mmol) of the Intermediate 5-c and 1.33 g (2.41 mmol) of theIntermediate 5-d were dissolved in 50.0 mL of tetrahydrofuran (THF).139.3 mg (0.12 mmol) of Pd(PPh3)₄ and 8.0 mL of an aqueous 5% K₂CO₃solution (by weight) were added to the solution and stirred at about120° C. for about 24 hours under reflux. After completion of thereaction, the temperature was cooled to room temperature, and 50.0 mL ofwater was added to stop the reaction. After extraction three times eachwith 70.0 mL of ethylacetate, the organic phase was collected and wasdried using magnesium sulfate and the solvent was evaporated. Theresidue was separated and purified by silica gel column chromatographyto obtain 0.8 g (1.27 mmol) of Compound 83 (Yield: 44.0%). This compoundwas identified using LC-MS. C44H22O2S2: M+ 647.10

Other compounds were further synthesized using the substituents of IGroup to VI groups above based on the equivalents and methods describedin the above synthesis examples.

LC-MS and NMR results of these compounds are summarized in the followingtable.

No. LC-MS ¹H NMR (CD₂Cl₂, 300 MHz) 1 C₃₂H₂₀N₂ • • • • 7.39 (m, 2H),7.42~7.61 (m, 4H), 7.82 (d, 2H, J = 7.79), M+ 433.20 7.86~7.85 (m, 6H),7.96 (d, 2H, J = 8.02), 8.01 (dd, 2H, J = 8.32) 2 C₄₀H₂₄N₂ • = 7.41 (d,1H, J = 8.23), 7.53 (d, 1H, J = 8.00), 7.60 (dd, 2H, J = 8.21), M+532.21 7.70 (dd, 2H, J = 9.37), 7.91 (dd, 2H, J = 2.43), 7.93 (d, 1H, J= 8.01), 7.95 (d, 1H, J = 2.51), 8.00~8.09 (m, 6H), 8.12 (dd, 2H, J =8.37), 8.23~8.26 (m, 4H) 3 C₄₄H₂₈N₂ • • = 7.41~7.50 (m, 2H), 7.59~7.63(m, 2H), 7.65~7.79 (m, 10H), M+ 585.24 7.96~8.04 (m, 4H), 8.08~8.32 (m,10H) 4 C₄₄H₂₈N₂ • • = 7.41 (dd, 2H, J = 8.33), 7.49~7.70 (m, 10H), 7.82(dd, 2H, M+ 585.24 J = 8.14), 7.85~7.92 (m, 4H), 7.92~7.96 (m, 4H), 8.01(dd, 2H, J = 8.36), 8.08 (dd, 2H, J = 7.45), 8.23 (dd, 2H, J = 1.91) 5C₃₀H₁₈N₄ • = 6.99 (dd, 2H, J = 6.64), 7.54 (dd, 2H, J = 8.31), 7.79 (dd,2H, M+ 435.17 J = 6.63), 7.91 (dd, 2H, J = 8.31), 7.97~8.00 (m, 6H),8.47~8.51 (m, 4H) 6 C₃₀H₁₈N₄ • = 7.60~7.61 (m, 4H), 7.91~7.99 (m, 8H),8.06 (dd, 2H, J = 8.37), M+ 435.19 8.36 (d, 2H, J = 2.51), 9.29 (d, 2H,J = 5.42) 7 C₂₈H₁₆N₂S₂ • • = 7.31 (d, 2H, J = 1.73), 7.55 (dd, 2H, J =8.54), 7.68 (dd, 2H, M+ 445.11 J = 6.42), 7.81~7.85 (m, 4H), 7.95 (dd,2H, J = 8.32), 8.06~8.07 (m, 4H) 8 C₂₈H₁₆N₂O₂ • • = 7.11 (d, 2H, J =1.72), 7.58~7.60 (m, 4H), 7.83~7.86 (m, 6H), M+ 413.14 8.06~8.07 (m, 4H)9 C₃₀H₂₀N₂S₂ • • = 7.27 (d, 1H, J = 7.85), 7.56~7.72 (m, 7H), 7.87 (dd,2H, J = 2.21), M+ 545.10 7.99~8.10 (m, 8H), 8.32 (dd, 2H, J = 7.48) 10C₃₆H₂₀N₂O₂ • • = 7.57~7.62 (m, 6H), 7.80 (dd, 2H, J = 6.62), 7.81~7.92(m, 4H), M+ 513.17 8.05~8.10 (m, 6H), 8.45 (d, 2H, J = 4.67) 11 C₃₈H₂₂N₄• • = 7.61~7.70 (m, 6H), 7.92 (d, 2H, J = 1.89), 8.01~8.14 (m, 10H), M+535.20 8.28 (dd, 2H, J = 6.45), 9.51 (dd, 1H, J = 4.91), 9.61 (dd, 1H, J= 5.40) 12 C₅₀H₃₆N₂ • = 2.08 (s, 6H), 7.12 (dd, 2H, J = 8.42), 7.29~7.32(m, 4H), 7.41 (d, M+ 1H, J = 8.47), 7.50 (dd, 2H, J = 1.75), 7.59 (d,1H, J = 7.55), 7.73~7.76 (m, 665.190 4H), 7.81~7.83 (m, 2H), 7.90 (m,4H), 7.97 (dd, 2H, J = 8.01), 8.04 (dd, 2H, J = 8.40) 13 C₅₆H₃₄N₄ • • =7.31 (dd, 1H, J = 7.52), 7.53 (t, 1H, J = 7.54), 7.57~7.64 (m, 6H), M+763.31 7.75 (dd, 2H, J = 8.76), 7.81~7.90 (m, 8H), 8.17 (dd, 2H, J =5.58), 8.23~8.26 (m, 4H), 8.30~8.36 (m, 6H), 8.52~8.58 (m, 4H) 14C₅₀H₃₀N₈ • • = 7.29 (m, 4H), 7.58 (dd, 2H, J = 7.57), 7.66~7.75 (m, 4H),M+ 743.29 7.94~8.03 (m, 12H), 8.12~8.18 (m, 4H), 8.29~8.32 (m, 4H) 15C₃₂H₁₀D₁₀N₂ • • = 7.31~7.33 (m, 2H), 7.47~7.52 (m, 2H), 7.65~7.70 (m,4H), M+ 443.22 7.78~7.84 (m, 2H) 16 C₃₆H₂₈N₂O₄ • • = 3.64 (s, 12H), 6.22(dd, 2H, J = 1.81), 7.13 (dd, 2H, J = 1.81), M+ 553.22 7.18 (dd, 2H, J =1.82), 7.62 (dd, 2H, J = 8.67), 7.85~8.04 (m, 8H) 17 C₄₄H₂₈N₂ • • = 7.41(dd, 2H, J = 7.32), 7.52~7.68 (m, 14H), 7.85~8.08 (m, M+ 585.24 10H),8.20 (d, 2H, J = 8.23) 18 C₃₆H₂₈N₂ • = 1.35 (t, 6H, J = 7.11), 4.62 (q,4H, J = 7.10), 7.41 (dd, 2H, J = 1.73), M+ 489.22 7.45~7.62 (m, 10H),7.81~7.92 (m, 6H) 19 C₃₂H₁₀F₁₀N₂ • • = 7.41 (t, 1H, J = 7.82), 7.59 (t,1H, J = 7.51), 7.86 (d, 2H, J = 2.18), M+ 613.10 7.91~8.02 (m, 6H), 20C₃₄H₂₆N₄ • • = 1.34 (t, 6H, J = 7.12), 4.59 (q, 4H, J = 7.10), 7.45 (dd,2H, M+ 491.23 J = 8.75), 7.62 (q, 2H, J = 1.73), 7.76 (dd, 2H, J =8.70), 7.85 (dd, 2H, J = 1.73), 7.92 (m, 2H), 8.10~8.19 (m, 4H),8.50~8.55 (m, 2H) 21 C₄₀H₂₄N₆ • • = 7.37~7.45 (m, 2H), 7.52 (dd, 2H, J =8.23), 7.58~7.64 (m, 4H), M+ 589.20 7.84 (dd, 2H, J = 8.22), 7.89~7.93(m, 4H), 8.03 (dd, 2H, J = 1.74), 8.05~8.08 (m, 4H), 8.24 (dd, 2H, J =8.23), 8.80 (dd, 2H, J = 1.99), 9.16 (dd, 2H, J = 1.99) 22 C₃₂H₂₄N₂S₂ •= 1.52 (t, 6H, J = 6.80), 4.59 (q, 4H, J = 6.81), 7.41 (dd, 2H, J =9.35), M+ 502.15 7.56~7.59 (m, 2H), 7.60~7.63 (m, 4H), 7.78 (dd, 2H, J =6.24), 7.83 (dd, 2H, J = 1.98), 7.90 (dd, 2H, J = 1.82) 23 C₄₈H₃₂N₂S₂ •• = 1.51 (t, 6H, J = 2.67), 4.88 (q, 4H, J = 2.66), 7.51 (t, 2H, J =5.98), M+ 701.22 7.75~7.86 (m, 8H), 7.95 (dd, 2H, J = 6.78), 8.24~8.35(m, 6H), 8.38~8.41 (m, 2H), 8.49~8.53 (m, 2H) 24 C₅₆H₃₂N₂O₂ • • =7.53~7.64 (m, 6H), 7.85 (dd, 2H, J = 5.03), 7.86 (dd, 2H, M+ 765.26 J =8.55), 7.88~7.93 (m, 2H), 7.96~8.21 (m, 12H), 8.34~8.37 (m, 2H),8.45~8.50 (m, 4H), 8.59~8.68 (m, 2H) 25 C₃₆H₂₈N₂ • • = 1.37 (t, 6H, J =7.13), 4.77 (q, 4H, J = 7.11), 7.45 (dd, 2H, M+ 489.24 J = 9.10), 7.47(t, 2H, J = 8.11), 7.53~7.63 (m, 8H), 7.70~7.74 (m, 2H), 7.76~7.79 (m,2H), 7.83~7.88 (m, 2H) 26 C₅₆H₃₂N₂S₂ • • = 7.56 (t, 2H, J = 6.31), 7.79(dd, 2H, J = 8.45), 7.92~8.06 (m, 8H), M+ 797.20 8.54 (dd, 2H, J-8.45),8.72~8.82 (m, 4H), 8.90~9.09 (m, 6H), 9.15~9.31 (m, 8H) 27 C₅₄H₄₄N₂ • •= 1.36 (t, 6H, J = 6.99), 2.11 (s, 12H), 5.17 (q, 4H, J = 6.99), M+721.37 7.31~7.37 (m, 2H), 7.51~7.65 (m, 8H), 7.74~7.79 (m, 6H),7.90~7.95 (m, 6H) 28 C₄₂H₂₆N₄ • • = 7.40~7.44 (m, 2H), 7.51~7.60 (m,6H), 7.71~7.79 (m, 2H), M+ 587.23 7.84 (dd, 2H), J = 8.22), 7.89~7.93(m, 4H), 7.99~8.08 (m, 6H), 8.63~8.66 (m, 2H), 9.13 (dd, 2H, J = 2.76)29 C₆₀H₄₂N₄ • • = 1.53 (t, 6H, J = 2.67), 5.28 (q, 4H, J = 2.67),7.49~7.60 (m, 8H), M+ 818.36 7.71 (dd, 2H, J = 7.22), 7.79~7.95 (m,10H), 8.16~8.29 (m, 4H), 8.39~8.47 (m, 6H), 8.83 (dd, 2H, J = 4.77) 30C₅₂H₃₂N₆ • • = 7.11~7.18 (m, 1H), 7.31~7.42 (m, 3H), 7.58~7.60 (m, 4H),M+ 741.28 7.61~7.63 (m, 2H), 7.82~7.86 (m, 4H), 7.91~8.06 (m, 10H),8.09~8.12 (m, 2H), 8.18~8.21 (m, 2H), 8.28~8.30 (m, 2H), 9.75 (d, 2H, J= 1.99) 31 C₅₂H₃₂N₆ • • = 7.26~7.34 (m, 5H), 7.57~7.64 (m, 4H),7.83~7.95 (m, 5H), M+ 741.28 8.06~8.16 (m, 10H), 8.28 (d, 2H, J = 1.51),8.58 (d, 2H, J = 8.46), 8.84 (dd, 2H, J = 1.99), 9.03~9.07 (m, 2H) 32C₄₄H₂₈N₂ • • = 7.49~7.78 (m, 14H), 7.91 (dd, 2H, J = 8.02), 7.95 (dd,2H, M+ 585.24 J = 2.23), 8.00~8.07 (m, 6H), 8.19~8.23 (m, 4H) 33C₅₆H₃₂N₂O₂ • • = 7.74~7.83 (m, 5H), 7.88~7.93 (m, 3H), 8.13~8.18 (m,2H), M+ 765.23 8.60 (dd, 2H, J = 5.04), 8.65~8.77 (m, 8H), 8.81~8.99 (m,12H) 34 C₅₄H₃₄N₄ • • = 7.54~7.61 (m, 2H), 7.74~7.80 (m, 4H), 7.87~7.93(m, 8H), M+ 739.29 8.07~8.09 (m, 2H), 8.12~8.17 (m, 6H), 8.23~8.29 (m,2H), 8.32~8.36 (m, 6H), 8.40~8.46 (m, 2H), 8.50~8.57 (m, 2H) 35 C₄₂H₂₆N₄• • = 7.50~7.70 (m, 12H), 8.00~8.06 (m, 4H), 8.15 (dd, 2H, M+ 587.23 J =8.44), 8.22~8.26 (m, 4H), 8.83~8.89 (m, 4H) 36 C₄₄H₂₈N₂ • • = 7.51 (dd,2H, J = 7.45), 7.54 (dd, 2H, J = 7.77), 7.60 (q, 4H, M+ 585.24 J =8.15), 7.61~7.67 (m, 6H), 7.90 (dd, 2H, J = 8.15), 7.92~8.04 (m, 8H),8.10 (dd, 2H, J = 8.49), 8.26 (dd, 2H, J = 8.48) 37 C₄₂H₂₆N₄ • • = 7.50(t, 1H, J = 7.79), 7.52 (t, 1H, J = 8.39), 7.55~7.64 (m, 4H), M+ 587.237.87~7.94 (m, 4H), 7.98 (dd, 2H, J = 8.51), 8.09~8.13 (m, 2H), 8.18~8.24(m, 5H), 8.5~8.29 (m, 2H), 8.37 (q, 2H, J = 8.49), 9.07~9.14 (m, 4H) 38C₄₄H₃₂N₂ • = 1.47 (t, 6H, J = 7.06), 4.63 (q, 4H, J = 7.05), 7.56 (dd,2H, J = 6.75), M+ 589.25 7.69~7.81 (m, 5H), 7.85 (dd, 1H, J = 6.58),7.88 (dd, 1H, J = 6.57), 7.90 (dd, 2H, J = 7.18), 8.06~8.10 (m, 4H),8.15~8.21 (m, 3H), 8.27~8.31 (m, 1H), 8.55~8.59 (m, 2H) 39 C₅₆H₂₈F₄N₂S₂• • = 7.32 (dd, 2H, J = 1.92), 7.71 (dd, 2H, J = 1.74), 7.78 (dd, 1H, M+869.15 J = 8.36), 7.83 (dd, 1H, J = 8.39), 8.01~8.14 (m, 6H), 8.32 (dd,2H, J = 8.38), 8.61~8.65 (m, 2H), 8.70~8.75 (m, 4H), 8.92~8.98 (m, 4H),9.05~9.10 (m, 4H) 40 C₅₂H₃₂N₆ • • = 7.38 (dd, 3H, J = 7.83), 7.51~7.58(m, 2H), 7.65 (dd, 1H, M+ 741.23 J = 8.40), 7.87 (dd, 2H, J = 6.78),7.91~7.93 (m, 4H), 8.11 (dd, 2H, J = 5.25), 8.18~8.35 (m, 11H), 8.40(dd, 1H, J = 6.21), 8.50 (dd, 2H, J = 6.92), 8.78~8.83 (m, 2H),9.40~9.44 (m, 2H) 41 C₄₄H₂₈N₂ • • = 7.30~7.34 (m, 2H), 7.60~7.73 (m,12H), 7.89~7.97 (m, 8H), M+ 585.22 8.01 (dd, 2H, J = 8.22), 8.06 (dd,2H, J = 8.44), 8.22 (dd, 2H, J = 8.44) 42 C₄₄H₃₀N₄O₂ • • = 3.80 (s, 6H),7.03 (dd, 4H, J = 8.72), 7.69~7.78 (m, 4H), M+ 647.22 7.81~7.90 (m, 3H),7.94 (dd, 1H, J = 8.70), 7.96 (dd, 2H, J = 1.99), 7.98 (dd, 2H, J =2.19), 8.05 (dd, 2H, J = 8.44), 8.26 (dd, 2H, J = 8.45), 8.45 (dd, 2H, J= 5.09), 9.35 (dd, 2H, J = 3.05) 43 C₄₈H₃₆N₂ • • = 1.50 (t, 6H, J =6.73), 4.60 (q, 4H, J = 6.73), 7.53~7.57 (m, 2H), M+ 641.30 7.60~7.71(m, 12H), 7.73~7.84 (m, 4H), 8.00~8.13 (m, 4H), 8.50~8.53 (m, 2H) 44C₅₆H₃₈N₄ • • = 6.88~6.92 (m, 8H), 7.19~7.39 (m, 16H), 7.53 (dd, 2H, J =1.81), M+ 767.25 7.55 (dd, 4H, J = 8.23), 7.82~7.96 (m, 8H) 45 C₅₆H₄₂N₄• • = 1.35 (t, 6H, J = 7.00), 4.54 (q, 4H, J = 7.00), 6.90~6.94 (m, 4H),M+ 771.30 7.14 (dd, 1H, J = 8.23), 7.16 (dd, 1H, J = 8.22), 7.19~7.49(m, 20H), 7.76~7.84 (m, 6H) 46 C₇₂H₄₈N₆ • • = 6.59~6.93 (m 8H),7.19~7.35 (m, 17H), 7.40~7.56 (m, 9H), M+ 997.40 7.60 (dd, 2H, J =8.40), 7.84~7.89 (m, 4H), 7.92~7.98 (m, 4H), 8.00~8.08 (m, 4H) 47C₅₆H₃₄N₄ • • = 7.29~7.33 (m, 1H), 7.53~7.66 (m, 13H), 7.88 (dd, 2H, J =8.58), M+ 763.29 8.02 (dd, 2H, J = 6.98), 8.11 (dd, 2H, J = 5.52),8.19~8.28 (m, 12H), 8.50 (dd, 2H, J = 4.40) 48 C₃₇H₂₁N₃S • • = 7.48~7.52(m, 1H), 7.60~7.63 (m, 1H), 7.69~7.84 (m, 4H), M+ 540.16 7.99~8.26 (m,12H), 8.33~8.35 (m, 1H), 8.42~8.45 (m, 1H), 8.69~8.73 (m, 1H) 49C₄₄H₂₉N₃ • • = 6.57~6.60 (m, 4H), 7.26~7.38 (m, 7H), 7.46~7.52 (m, 4H),M+ 600.24 7.69 (dd, 2H, J = 7.93), 7.77 (dd, 1H, J = 8.66), 7.84~7.90(m, 3H), 8.01 (dd, 2H, J = 8.45), 8.08 (dd, 2H, J = 7.88), 8.12~8.20 (m,4H) 50 C₅₀H₂₉N₃S • • = 7.31~7.36 (m, 1H), 7.68~7.77 (m, 5H), 7.80~7.92(m, 6H), M+ 704.21 8.80 (dd, 1H, J = 5.54), 8.09~8.37 (m, 13H), 8.39(dd, 1H, J = 5.34), 8.64~8.70 (m, 1H) 51 C₄₁H₂₅N₅ • • = 7.44 (t, 1H, J =7.78), 7.51 (dd, 1H, J = 8.23), 7.54 (dd, 1H, M+ 588.20 J = 8.23),7.60~7.72 (m, 6H), 7.86~8.09 (m, 12H), 8.10~8.24 (m, 4H) 52 C₅₄H₃₄N₄ • •= 7.48 (t, 2H, J = 7.43), 7.53 (dd, 2H, J = 8.55), 7.59~7.64 (m, 8H), M+739.28 7.68~7.73 (m, 4H), 7.88 (dd, 2H, J = 7.89), 7.92 (dd, 2H, J =8.00), 7.99 (dd, 2H, J = 1.76), 8.06~8.14 (m, 4H), 8.19~8.25 (m, 4H),8.42~8.46 (m, 2H), 9.19~9.24 (m, 2H) 53 C₆₁H₃₇N₅ • • = 7.35~7.41 (m,2H), 7.65~7.70 (m, 1H), 7.74 (dd, 1H, J = 7.75), M+ 840.32 7.80~8.01 (m,11H), 8.05~8.09 (m, 6H), 8.12 (dd, 2H, J = 3.76), 8.20~8.25 (m, 4H),8.28~8.30 (m, 2H), 8.46~8.50 (m, 2H), 8.55~8.58 (m, 1H), 8.66~8.71 (m,3H), 8.83~8.85 (m, 1H), 9.49~9.52 (m, 1H) 54 C₅₃H₄₃N₅ • • = 1.62 (s,9H), 1.63 (s, 9H), 7.35~7.42 (m, 2H), 7.46~7.57 (m, M+ 750.35 3H),7.68~7.72 (m, 1H), 7.80~7.99 (m, 8H), 8.09~8.20 (m, 4H), 8.29~8.34 (m,1H) 8.65~8.71 (m, 2H), 8.90~8.95 (m, 1H), 9.32~9.36 (m, 1H), 9.38 (dd,1H, J = 5.04) 55 C₆₀H₄₀N₂S₂ • • = 2.11 (t, 6H, J = 6.94), 4.82 (q, 4H, J= 6.93), 7.60~7.63 (m, 2H), M+ 853.24 7.69~7.76 (m, 6H), 7.95~7.98 (m,2H), 8.02~8.07 (m, 3H), 8.14~8.17 (m, 1H), 8.29~8.32 (m, 2H), 8.64 (dd,2H, J = 5.47), 8.69 (dd, 2H, J = 5.00), 8.71~8.75 (m, 4H), 8.85 (d, 2H,J = 5.13), 9.02 (dd, 2H, J = 5.47), 9.09 (dd, 2H, J = 5.47) 56 C₄₃H₂₇N₃• = 7.39~7.45 (m, 2H), 7.47~7.52 (m, 1H), 7.58 (t, 1H, J = 8.02), M+586.22 7.60~7.65 (m, 5H), 7.70~7.73 (m, 1H), 7.80~7.85 (m, 2H),7.89~7.93 (m, 5H), 7.99~8.08 (m, 3H), 8.19~8.24 (m, 1H), 8.30 (q, 1H, J= 1.93), 8.36 (dd, 1H, J = 1.82), 8.62~8.65 (m, 1H) 57 C₄₆H₂₈N₄ • =7.29~7.37 (m, 2H), 7.52 (dd, 1H, J = 8.23), 7.56 (dd, 1H, J = 7.89), M+637.24 7.58~7.72 (m, 5H), 7.82~7.86 (m, 2H), 7.90~7.92 (m, 1H),7.93~7.95 (m, 3H), 7.98~8.03 (m, 1H), 8.06 (dd, 1H, J = 7.87), 8.09~8.14(m, 1H), 8.17 (dd, 1H, J = 6.45), 8.20~8.25 (m, 3H), 8.28~8.33 (m, 3H),8.43~8.45 (m, 1H), 8.51~8.55 (m, 1H) 58 C₄₀H₂₄N₂ • • = 7.31~7.38 (m,6H), 7.49 (dd, 2H, J = 8.82), 7.52 (dd, 2H, J = 8.47), M+ 533.197.58~7.66 (m, 12H), 7.71~7.73 (m, 2H) 59 C₄₈H₃₄N₄ • • = 1.64 (t, 6H, J =2.67), 5.19 (q, 4H, J = 2.66), 7.30~7.35 (m, 2H), M+ 667.29 7.53~7.55(m, 2H), 7.58~7.65 (m, 4H), 7.70~7.77 (m, 2H), 7.82~7.84 (m, 1H),7.91~8.06 (m, 9H), 8.32~8.38 (m, 4H) 60 C₃₈H₂₂N₄ • • = 7.32~7.38 (m,2H), 7.50~7.54 (m, 4H), 7.59~7.65 (m, 4H), M+ 535.20 7.66 (dd, 1H, J =7.80), 7.74 (dd, 1H, J = 7.80), 7.78~7.84 (m, 4H), 7.90~7.94 (m, 4H),9.27~9.32 (m, 2H) 61 C₄₂H₂₄N₂O • • = 6.80~6.82 (m, 1H), 7.13~7.16 (m,1H), 7.26~7.39 (m, 4H), M+ 573.20 7.44~7.75 (m, 16H), 7.86 (dd, 1H, J =8.83), 8.10~8.13 (m, 1H) 62 C₅₂H₃₂N₂ • • = 7.19~7.24 (m, 2H), 7.31~7.34(m, 2H), 7.38~7.42 (m, 4H), M+ 685.27 7.46~7.69 (m, 16H), 7.75 (dd, 2H,J = 1.91), 7.79~7.84 (m, 4H), 7.94~7.98 (m 2H) 63 C₅₈H₃₄N₄ • • =7.19~7.21 (t, 1H, J = 7.83), 7.32~7.37 (m, 1H), 7.49~7.70 (m, M+ 787.2914H), 7.86~7.95 (m, 4H), 8.03~8.10 (m, 6H), 8.28~8.32 (m, 2H), 8.42 (dd,2H, J = 5.64), 8.48 (dd, 2H, J = 5.64), 8.78~8.80 (m, 2H) 64 C₅₈H₄₀N₆ •= 2.01 (t, 6H, J = 6.95), 5.30 (q, 4H, J = 6.95), 7.60~7.68 (m, 5H), M+821.35 7.74~7.78 (m, 1H), 7.92~7.95 (m, 4H), 8.31~8.33 (m, 1H),8.48~8.50 (m, 4H), 8.53~8.58 (m, 1H), 8.60~8.65 (m, 5H), 8.69 (dd, 1H, J= 5.28), 8.70 (dd, 1H, J = 5.26), 8.80~8.82 (m, 2H), 9.07~9.10 (m, 2H),9.10~9.14 (m, 2H) 65 C₅₆H₄₀F₂N₄ • = 1.07 (t, 6H, J = 7.03), 4.53 (q, 4H,J = 7.03), 6.97 (dd, 2H, J = 8.90), M+ 807.34 7.00 (dd, 2H, J = 8.75),7.16~7.36 (m, 22H), 7.58~7.64 (m, 4H) 66 C₅₈H₄₆N₄O₂ • • = 1.39 (t, 6H,7.11) 3.80 (s, 6H), 4.79 (q, 4H, J = 7.10), 6.46 (dd, M+ 831.38 2H, J =8.53), 6.99 (d, 1H, J = 8.42), 7.02 (d, 1H, J = 8.46), 7.17~7.30 (m,15H), 7.37 (dd, 2H, J = 1.80), 7.56 (dd, 1H, J = 3.17), 7.57~7.62 (m,6H), 7.95 (dd, 1H, J = 8.53), 8.13~8.16 (m, 1H) 67 C₄₆H₂₆N₂S • • =7.33~7.38 (m, 3H), 7.48 (dd, 2H, J = 8.83), 7.50 (dd, 1H, J = 8.82), M+639.20 7.53~7.69 (m, 14H), 7.73~7.79 (m, 3H), 7.84~7.89 (m, 1H), 8.06(dd, 1H, J = 7.74), 8.12 (dd, 1H, J = 3.75) 68 C₆₄H₄₆N₄S₂ • • = 1.76 (t,6H, J = 6.80), 2.20 (t, 6H, J = 6.94), 5.10 (q, 4H, J = 6.94), M+ 935.335.23 (q, 4H, J = 6.80), 8.08~8.14 (m, 3H), 8.41~8.43 (m, 2H), 8.47~8.51(m, 3H), 8.56 (dd, 2H, J = 5.14), 8.66 (dd, 2H, J = 5.13), 8.69~8.8.86(m, 11H), 8.92~8.95 (m, 3H), 9.04~9.10 (m, 2H) 69 C₄₈H₃₈N₄O₂ • • = 1.54(t, 6H, J = 2.67), 1.72 (t, 6H, J = 2.66), 4.90 (q, 4H, J = 2.67), M+703.32 5.02 (q, 4H, J = 2.66), 6.84 (dd, 2H, J = 3.00), 6.92 (dd, 2H, J= 2.99), 7.44~7.51 (m, 4H), 7.70~7.77 (m, 4H), 7.87 (dd, 1H, J = 5.88),8.05 (dd, 1H, J = 5.81), 8.19 (d, 1H, J = 5.21), 8.39 (d, 1H, J = 5.53),8.47 (d, 1H, J = 4.08), 8.83 (d, 1H, J = 4.37) 70 C₃₂H₁₈S₂ • • = 7.49(t, 2H, J = 7.76), 7.67~7.80 (m, 8H), 8.06 (dd, 2H, J = 7.01), M+ 467.088.12~8.16 (m, 2H), 8.61 (dd, 2H, J = 5.77), 8.78 (dd, 2H, J = 1.82) 71C₄₄H₂₆S₂ • • • 7.33~7.38 (m, 2H), 7.48 (dd, 2H, J = 8.83), 7.51~7.69 (m,14H), M+ 619.15 7.73~7.79 (m, 4H), 7.84~7.89 (m, 2H), 8.06 (dd, 1H, J =7.74), 8.12 (dd, 1H, J = 3.75) 72 C₄₀H₂₂S₂ • • = 7.61~7.70 (m, 6H), 7.91(d, 2H, J = 1.89), 8.01~8.12 (m, 10H), M+ 567.12 8.30 (dd, 2H, J =6.45), 9.49 (dd, 2H, J = 4.91) 73 C₅₀H₃₄S₂ • • = 7.53 (dd, 2H, J =7.54), 7.57~7.62 (m, 6H), 7.71 (dd, 2H, J = 8.75), M+ 699.20 7.81~7.90(m, 8H), 8.16 (dd, 2H, J = 5.58), 8.23~8.26 (m, 4H), 8.30~8.60 (m, 10H)74 C₄₄H₂₂S₄ • • = 7.35~7.54 (m, 6H), 7.59~7.65 (m, 4H), 7.69 (dd, 2H, J= 7.58), M+ 679.05 7.81~7.92 (m, 8H), 9.27~9.32 (m, 2H) 75 C₃₀H₁₆N₂S₂ •• = 7.43 (dd, 2H, J = 1.70), 7.51 (dd, 2H, J = 8.55) 7.71~7.85 (m, 6H),M+ 469.08 7.95 (dd, 2H, J = 8.32), 8.06~8.07 (m, 4H) 76 C₅₆H₃₂N₂S₂ • • =7.49~7.55 (m, 6H), 7.83~7.93 (m, 4H), 7.96~8.08 (m, 12H), M+ 797.208.21~8.25 (m, 2H), 8.35~8.40 (m, 4H), 8.59~8.68 (m, 2H) 77 C₃₆H₂₀N₂S₂ •• = 7.44~7.52 (m, 6H), 7.80~7.90 (m, 6H), 8.05~8.10 (m, 6H), M+ 545.108.45 (d, 2H, J = 4.67) 78 C₅₀H₂₈N₆S₂ • = 7.30~7.35 (m, 2H), 7.54~7.72(m, 7H), 7.82~7.86 (m, 2H), M+ 777.19 7.93~8.08 (m, 6H), 8.17 (dd, 2H, J= 6.45), 8.20~8.33 (m, 6H), 8.43~8.45 (m, 1H), 8.51~8.55 (m, 1H) 79C₄₀H₂₂S₄ • • = 7.51~7.61 (m, 6H), 7.83~7.88 (m, 2H), 7.93 (dd, 2H, J =7.44), M+ 630.07 8.05~8.10 (m, 8H), 8.57 (d, 2H, J = 4.71) 80 C₄₆H₂₆N₄S₂• • = 7.55~7.68 (m, 10H), 7.94~8.03 (m, 6H), 8.11 (dd, 2H, J = 8.03), M+699.15 8.23 (dd, 2H, J = 5.32), 8.29~8.31 (m, 2H), 8.77 (dd, 2H, J =4.99), 8.85 (dd, 2H, J = 4.97) 81 C₄₄H₂₈N₂S₂ • • = 7.51~7.78 (m, 12H),7.82~8.02 (m, 12H), 8.08 (dd, 2H, J = 7.45), M+ 649.17 8.23 (dd, 2H, J =1.91) 82 C₃₂H₁₄F₄S₂ • • = 7.48 (dd, 2H, J = 8.76), 7.60 (dd, 2H, J =8.76), 7.73~7.79 (m, 4H), M+ 539.05 8.09 (d, 2H, J = 4.51), 8.11 (dd,2H, J = 7.33), 8.60~8.64 (m, 2H) 83 C₄₄H₂₂O₂S₂ • • = 8.27~8.31 (m, 2H),8.93~9.00 (m, 6H), 9.04~9.10 (m, 8H), M+ 647.11 9.20 (d, 2H, J = 4.86),9.28 (dd, 2H, J = 5.02), 9.34~9.37 (m, 2H) 84 C₄₀H₂₂N₄S₂ • • = 7.92~8.05(m, 6H), 8.24 (d, 2H, J = 4.04), 8.43 (dd, 2H, J = 5.63), M+ 623.138.66~8.74 (m, 4H), 9.04~9.10 (m, 4H), 9.51~9.55 (m, 4H) 85 C₃₂H₁₈N₄S₂ •• = 6.47~6.52 (m, 4H), 6.67 (s, 2H), 7.18 (dd, 2H, J = 3.09), M+ 523117.82 (dd, 2H, J = 7.84), 7.98 (d, 2H, J = 1.01), 8.12~8.20 (m, 4H), 8.43(s, 2H) 86 C₂₈H₂₆S₂ • • = 1.45 (s, 18H), 7.51 (dd, 2H, J = 8.56),7.76~7.80 (m, 2H), M+ 427.14 8.04 (d, 2H, J = 1.86), 8.16 (dd, 2H, J =8.56) 87 C₅₂H₃₂N₂S₂ • • = 7.23~7.42 (m, 4H), 7.58~7.63 (m, 6H),7.83~7.87 (m, 4H), M+ 749.21 7.91~8.13 (m, 6H), 8.19~8.21 (m, 2H),8.28~8.30 (m, 2H), 9.75 (d, 2H, J = 1.99) 88 C₄₂H₂₄N₂S₂ • • = 7.12~7.16(m, 2H), 7.26~7.39 (m, 4H), 7.44~7.75 (m, 16H), M+ 620.11 7.86 (dd, 1H,J = 8.79), 8.10~8.13 (m, 1H) 89 C₃₂H₁₆F₂S₂ • • = 7.54~7.78 (m, 8H), 8.13(d, 2H, J = 8.50), 8.26 (d, 2H, M+ 503.05 J = 5.58), 8.42 (dd, 2H, J =8.50), 8.54 (dd, 2H, J = 5.58) 90 C₄₀H₂₂N₄S₂ • • = 7.05~7.09 (m, 2H),7.21~7.30 (m, 4H), 7.50~7.78 (m, 14H), M+ 623.11 7.90 (dd, 1H, J =5.43), 8.10~8.13 (m, 1H) 91 C₂₈H₁₄O₂S₂ • • = 6.47~6.52 (m, 2H), 6.67 (s,2H), 7.82 (dd, 2H, J = 7.84), M+ 447.05 7.98 (d, 2H, J = 1.01),8.12~8.20 (m, 4H), 8.43 (s, 1H) 92 C₃₈H₂₀N₂S₂ • • = 7.94~8.02 (m, 4H),8.43~8.45 (m, 2H), 8.49 (d, 2H, J = 6.80), M+ 569.10 8.55 (d, 2H, J =6.80), 8.61~8.74 (m, 6H), 9.15 (dd, 2H, J = 5.05), 9.38~9.42 (m, 2H) 93C₄₄H₂₆S₂ • • = 7.35~7.48 (m, 6H), 7.58~7.71 (m, 14H), 7.84~7.92 (m, 4H),M+ 619.15 8.06 (dd, 1H, J = 7.74), 8.12 (dd, 1H, J = 3.75) 94C₄₂H₂₀F₄N₂S₂ • • = 7.41~7.51 (m, 6H), 7.69~7.79 (m, 8H), 7.91~7.95 (m,4H), M+ 693.09 8.21 (dd, 2H, J = 5.32) 95 C₅₆H₃₆N₂S₂ • • = 7.18~7.22 (m,6H), 7.28~7.34 (m, 8H), 7.43~7.46 (m, 6H), M+ 801.22 7.48~7.52 (m, 4H),7.54~7.63 (m, 6H), 7.76 (dd, 2H, J = 4.38), 7.93 (dd, 2H, J = 8.32),8.69 (dd, 2H, J = 8.32) 96 C₄₈H₂₆O₂S₂ • • = 7.33~7.38 (m, 3H), 7.48~7.50(m, 2H), 7.57~7.70 (m, 14H), M+ 699.14 7.74~7.89 (m, 4H), 8.06 (dd, 1H,J = 7.74), 8.12 (dd, 1H, J = 3.75) 97 C₄₀H₂₂S₄ • • = 7.44~7.52 (m, 6H),7.63~7.75 (m, 2H), 8.05 (dd, 2H, J = 5.32), M+ 631.05 8.10~8.19 (m, 8H),8.43 (d, 2H, J = 5.33) 98 C₆₂H₄₂S₂ • • = 2.85 (s, 12H), 7.58~7.72 (m,6H), 7.81~7.90 (m, 6H), M+ 851.27 8.07~8.10 (m, 2H), 8.27~8.31 (m, 6H),8.51~8.54 (m, 4H), 8.86~8.90 (m, 4H), 9.10 (dd, 2H, J = 5.49) 99C₅₄H₂₈N₂O₂S₂ • • = 8.01 (dd, 2H, J = 8.62), 8.17~8.20 (m, 2H), 8.96~9.17(m, M+ 801.15 16H), 9.34~9.42 (m, 6H), 9.63 (dd, 2H, J = 5.35) 100C₃₆H₃₀O₂S₂ • • = 1.88 (s, 18H), 6.66 (dd, 2H, J = 2.80), 7.10 (dd, 2H, J= 2.81), M+ 559.15 7.65 (d, 1H, J = 1.75), 7.90 (d, 1H, J = 1.75), 8.42(d, 2H, J = 5.50), 8.54 (d, 2H, J = 8.03), 9.04 (dd, 2H, J = 5.50) 101C₄₆H₂₀F₁₀O₂S₂ • • = 4.13 (s, 6H), 7.14~7.18 (m, 4H), 7.56~7.60 (m, 2H),M+ 859.05 7.71~7.74 (m, 2H), 8.08 (d, 2H, J = 5.35), 8.38 (d, 2H, J =5.15), 8.64 (dd, 2H, J = 5.51) 102 C₃₈H₂₀N₂O₂S₂ • • = 4.13 (s, 6H),7.14~7.18 (m, 4H), 7.56~7.60 (m, 2H), M+ 601.10 7.71~7.74 (m, 2H), 8.08(d, 2H, J = 5.35), 8.38 (d, 2H, J = 5.15), 8.64 (dd, 2H, J = 5.51) 103C₄₆H₃₆N₂O₂S₂ • • = 2.30 (s, 18H), 6.76 (dd, 2H, J = 4.03), 6.95 (dd, 2H,J = 4.03), M+ 713.22 7.73~7.76 (m, 2H), 7.98 (dd, 2H, J = 1.75),8..70~8.83 (m, 6H), 9.26 (d, 4H, J = 5.07) 104 C₃₀H₁₆OS₂ • • = 7.62~7.76(m, 8H), 7.99 (dd, 2H, J = 1.82), 8.10~8.13 (m, 2H), M+ 457.05 8.56 (dd,2H, J = 1.83), 8.75 (dd, 2H, J = 1.82) 105 C₃₈H₂₀S₃ • • = 7.90~7.95 (m,4H), 8.41~8.43 (m, 2H), 8.50 (d, 2H, J = 8.23), M+ 573.07 8.53 (d, 2H, J= 6.80), 8.60~8.69 (m, 6H), 9.14~9..39 (m, 4H) 106 C₃₈H₂₃NS₂ • • =7.18~7.34 (m, 7H), 7.40 (dd, 1H, J = 8.54), 7.57~7.69 (m, 8H), M+ 558.137.84~7.90 (m, 1H), 8.01 (dd, 1H, J = 6.12), 8.19 (dd, 1H, J = 7.38),8.24~8.30 (m, 2H), 8.38 (dd, 1H, J = 7.53) 107 C₃₈H₂₃NS₂ • • = 7.16~7.25(m, 6H), 7.33 (dd, 1H, J = 8.49), 7.56~7.70 (m, 8H), M+ 558.12 7.85~7.92(m, 2H), 8.07 (dd, 1H, J = 8.12), 8.19 (dd, 1H, J = 6.75), 8.31~8.35 (m,2H), 8.71 (dd, 1H, J = 2.11) 108 C₂₉H₁₅NOS₂ • • = 6.68 (dd, 1H, J =2.79), 7.28 (dd, 1H, J = 2.79), 7.54~7.60 (m, M+ 458.05 1H), 8.17 (d,1H, J = 4.97), 8.18~8.21 (m, 1H), 8.86~8.89 (m, 1H), 8.94~8.90 (m, 5H),9.12 (dd, 1H, J = 5.08), 9.27~9.30 (m, 1H), 9.50~9.52 (m, 1H) 109C₃₈H₁₈F₂S₃ • • = 6.45~6.49 (m, 4H), 6.64 (dd, 2H, J = 4.01), 7.15 (dd,2H, M+ 609.05 J = 3.91), 7.79 (dd, 2H, J = 4.08), 7.98 (d, 2H, J =1.01), 8.10~8.15 (m, 4H), 8.38 (m, 2H) 110 C₄₄H₃₃NS₂ • • = 1.48 (t, 3H,J = 2.67), 2.21 (s, 9H), 5.11 (q, 2H, J = 2.67), M+ 640.21 7.33 (dd, 1H,J = 7.56), 7.64~7.70 (m, 2H), 7.81~7.89 (m, 2H), 8.34~8.42 (m, 2H),8.47~8.51 (m, 2H), 8.72 (dd, 1H, J = 7.56), 8.80~8.86 (m, 2H), 8.94 (d,1H, J = 5.08), 9.06~9.23 (m, 5H) 111 C₄₂H₃₁NOS₂ • • = 1.45 (t, 3H, J =3.11), 2.19 (s, 9H), 5.05 (q, 2H, J = 3.15), M+ 630.18 7.31 (dd, 1H, J =7.56), 7.64~7.70 (m, 2H), 7.79~7.85 (m, 2H), 8.29~8.31 (m, 2H), 8.56(dd, 1H, J = 3.15), 8.79~8.81 (m, 2H), 8.94~9.06 (m, 6H) 112 C₄₆H₃₀O₂S₂• • = 2.23 (s, 9H), 7.35 (dd, 1H, J = 4.33), 7.55~7.60 (m, 2H), M+679.17 7.75~7.80 (m, 4H), 8.33~8.35 (m, 2H), 8.55~8.58 (m, 2H), 8.71(dd, 2H, J = 4.10), 8.80~8.85 (m, 2H), 9.09~9.15 (m, 6H) 113 C₃₆H₁₈O₂S₂• • = 6.72 (dd, 1H, J = 3.86), 7.26 (dd, 1H, J = 3.86), 7.95~8.09 (m, M+547.07 3H), 8.21~8.25 (m, 1H), 8.68~8.71 (m, 1H), 8.98~9.03 (m, 7H),9.15 (dd, 1H, J = 5.07), 9.29~9.31 (m, 1H) 114 C₃₈H₂₁N₃S₂ • • =7.52~7.68 (m, 6H), 7.80~7.84 (m, 1H), 7.91 (d, 1H, J = 7.67), M+ 584.128.05~8.23 (m, 4H), 8.35 (dd, 1H, J = 8.44), 8.44 (d, 1H, J = 8.44), 8.53(d, 1H, J = 5.54), 8.60 (dd, 1H, J = 6.83), 8.63~8.68 (m, 2H), 8.82 (dd,1H, J = 5.42), 8.88 (dd, 1H, J = 5.54), 9.13~9.15 (m, 1H) 115 C₃₇H₂₂N₂S₂• • = 7.22~7.28 (m, 2H), 7.45~7.51 (m, 4H), 7.59~7.62 (m, 4H), M+ 559.127.66 (dd, 1H, J = 3.52), 7.70 (dd, 1H, J = 3.52), 7.78~7.85 (m, 4H),7.91~7.94 (m, 4H), 9.30~9.34 (m, 2H) 116 C₄₇H₃₁NS₂ • • = 2.35 (s, 6H),7.19~7.45 (m, 11H), 7.55~7.70 (m, 7H), M+ 674.19 7.99 (dd, 1H, J =1.99), 8.09~8.16 (m, 2H), 8.28~8.29 (m, 1H), 8.55~8.58 (m, 1H), 8.60 (d,1H, J = 0.77) 117 C₄₄H₂₈N₂S₂ • • = 7.31 (dd, 2H, J = 1.85), 7.72 (dd,2H, J = 1.85), 7.79 (dd, 1H, M+ 649.17 J = 2.01), 7.85 (dd, 1H, J =8.39), 8.01~8.15 (m, 6H), 8.33 (dd, 2H, J = 8.38), 8.53~8.58 (m, 2H),8.68~8.72 (m, 4H), 8.94~8.97 (m, 4H), 9.08~9.11 (m, 4H) 118 C₃₆H₁₈S₆ • •= 7.49~7.55 (m, 3H), 7.61~7.65 (m, 4H), 7.84~7.89 (m, 2H), M+ 642.978.09~8.14 (m, 3H), 8.72 (s, 1H), 8.73 (d, 2H, J = 1.82), 8.79 (d, 2H, J= 4.96), 8.98 (dd, 1H, J = 5.16) 119 C₃₆H₁₈O₄S₂ • • = 7.35~7.44 (m, 3H),7.55~7.60 (m, 4H), 7.70~7.79 (m, 2H), M+ 579.06 8.00~8.12 (m, 3H), 8.55(s, 1H), 8.65 (d, 2H, J = 8.41), 8.77 (d, 2H, J = 8.41), 8.85 (dd, 1H, J= 8.35) 120 C₅₅H₃₄N₂S₂ • • = 4.31 (s, 3H), 7.45~7.50 (m, 1H), 7.63~7.71(m, 3H), M+ 787.22 7.80~7.82 (m, 1H), 7.90~8.08 (m, 15H), 8.86~8.98 (m,6H), 9.08~9.13 (m, 3H), 9.20~9.22 (m, 2H) 121 C₆₀H₃₆N₂S₂ • • = 7.33~7.39(m, 2H), 7.45~7.51 (m, 4H), 7.75~7.80 (m, 2H), M+ 849.23 7.92~8.10 (m,16H), 8.75~8.80 (m, 6H), 9.01~9.11 (m, 4H), 9.19~9.23 (m, 2H) 122C₆₀H₃₆N₂S₂ • • = 7.63~7.70 (m, 4H), 7.98~8.03 (m, 8H), 8.36~8.40 (m,8H), M+ 849.21 8.54~8.58 (m, 4H), 8.90~8.95 (m, 2H), 9.03~9.05 (m, 2H),9.21~9.28 (m, 4H), 9.53~9.59 (m, 4H) 123 C₆₈H₄₀N₂S₄ • • = 7.68~7.73 (m,4H), 8.00~8.05 (m, 8H), 8.40~8.43 (m, 8H), M+ 1012.21 8.60~8.65 (m, 4H),8.75~8.79 (m, 4H) 8.91~8.96 (m, 2H), 9.10~9.16 (m, 2H), 9.20~9.27 (m,4H), 9.49~9.53 (m, 4H) 124 C₄₄H₂₂S₄ • • = 8.82~8.91 (m, 8H), 8.96~9.00(m, 2H), 9.02~9.04 (m, 1H), M+ 679.06 9.16~9.20 (m, 2H), 9.24~9.28 (m,1H), 9.32~9.40 (m, 8H) 125 C₃₆H₁₈O₂S₂ • • = 6.70 (dd, 2H, J = 4.18),7.29 (dd, 2H, J = 4.18), 8.06 (dd, 2H, M+ 547.07 J = 1.75), 8.73~8.75(m, 2H), 8.82~8.85 (m, 2H), 9.21 (d, 2H, J = 5.06), 9.31~9.42 (m, 6H)126 C₄₆H₂₄N₂O₂S₂ • • = 6.59 (dd, 2H, J = 4.41), 7.84 (dd, 2H, J = 4.41),8.09 (dd, 2H, M+ 701.13 J = 1.75), 8.65~8.68 (m, 2H), 8.73~8.78 (m, 4H),8.82~8.88 (m, 6H), 9.34~9.39 (m, 4H), 9.41 (s, 2H)

Example 1

To manufacture an anode, a corning 15 Ω/cm² (1200 Å) ITO glass substratewas cut to a size of 50 mm×50 mm×0.7 mm and then sonicated in isopropylalcohol and pure water each for live minutes, and then cleaned byirradiation of ultraviolet rays for 30 minutes and exposure to ozone.The resulting glass substrate was loaded into a vacuum depositiondevice.

Then, 2-TNATA, which is a HIL material, was vacuum-deposited on theglass substrate to form a HIL having a thickness of about 600 Å. Then,4,4′-bis[N-(1-naphthyl)-N-phenylamino-]biphenyl (NPB), which is a holetransporting compound, was vacuum-deposited on the HIL to form a HTLhaving a thickness of about 300 Å.

A blue fluorescent host 9,10-di-naphthalene-2-yl-anthracene (DNA) and ablue fluorescent dopant 1,4-bis-(2,2-diphenylvinyl)biphenyl (DPV81),which are both widely known compounds, were deposited at the same timeon the HTL in a weight ratio of 98:2 to form an EML having a thicknessof 300 Å.

Then, Compound 3 was deposited on the EML to form an ETL, and then LiF,which is a halogenated alkali metal, was deposited on the ETL to form anEIL having a thickness of 10 Å. Then, Al was vacuum-deposited on the EILto form a cathode having a thickness of 3000 Å, thereby forming a LiF/Alelectrode and completing the manufacture of an organic light-emittingdevice.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 14 was used, instead of Compound 3,to form the ETL.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 34 was used, instead of Compound 3,to form the ETL.

Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 51 was used, instead of Compound 3,to form the ETL.

Example 5

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 24 was used, instead of the knownhost DNA, to form the EML, and a widely-known Alq3 was used to form anETL on the EML.

Example 6

An organic light-emitting device was manufactured in the same manner asin Example 5, except that Compound 26 was used, instead of Compound 24,to form the EML.

Example 7

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 1 was used, instead of the widelyknown NPB, to form the HTL, and a blue fluorescent host9,10-di-naphthalene-2-yl-anthracene (DNA) and a blue fluorescent dopant1,4-bis-(2,2-diphenylvinyl)biphenyl (DPVBi), which are both widely knowncompounds, were deposited at the same time on the HTL in a weight ratioof 98:2 to form an EML having a thickness of 300 Å.

Example 8

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound 13 was used, instead of Compound 1,to form the HTL.

Example 9

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound 44 was used, instead of Compound 1,to form the HTL.

Example 10

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 26 was used as a blue fluorescenthost to form the EML, and Compound 34 was used to form the ETL.

Example 11

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound 51 was used, instead of Compound 34,to form the ETL.

Example 12

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 13 was used to form the HTL, Compound26 was used as a blue fluorescent host to form the EML, and Compound 3was used, instead of Alq3, to form the ETL.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that a widely known blue fluorescent host9,10-di-naphthalene-2-yl-anthracene (DNA) was used, instead of Compound7, to form the EML.

When the heterocyclic compounds of Formula 1 wherein X₁ and X₂ are—N(R₂₀)— were used as a HTL material, a host in EML, and/or an ETLmaterial of an organic light-emitting device, driving voltages werelower by about 1V or greater than those of the organic light-emittingdevices in which the widely-known material 2-TNATA, DNA, NPB, and/orAlq3 was used. In addition, good I-V-L characteristics with improvedefficiency, and remarkable improvements in luminance and lifetime wereattained. The organic light-emitting devices of Example 1-4 includingthe heterocyclic compounds of Formula 1 as ETL materials are found tohave higher efficiencies and longer lifetimes than the organiclight-emitting device of Comparative Example 1. The organiclight-emitting devices of Examples 5-6 including the heterocycliccompounds of Formula 1 as hosts are found to have lower driving voltagesby about 1.5V or greater, higher efficiencies by about 150% or greater,and longer lifetimes than the organic light-emitting device ofComparative Example 1. The organic light-emitting devices of Examples7-9 including the heterocyclic compounds of Formula 1 as HTL materialsare found to have lower driving voltages by about 1.0V or greater thanthe organic light-emitting device of Comparative Example 1. The organiclight-emitting devices of Examples 10-11 including the heterocycliccompounds of Formula 1 as a host or an ETL material are found to havelower driving voltages by about 1.4V or greater, higher efficiencies,and longer lifetimes than the organic light-emitting device ofComparative Example 1. The organic light-emitting device of Example 12including the heterocyclic compounds of Formula 1 as a HTL material, ahost of an EML, and an ETL material are found to have a lower drivingvoltage by about 2.1V, a higher efficiency by about 200%, and a longerlifetime by about 100% or greater than the organic light-emitting deviceof Comparative Example 1. The characteristics of the organiclight-emitting devices of Examples 1-12 and Comparative Example 1 areshown in Table 1 below.

TABLE 1 EML, HTL, Driving Current Half or ETL voltage density LuminanceEfficiency Luminescent life-span material (V) (mA/cm²) (cd/m²) (cd/A)color (hr @100 mA/cm²) Example 1 Compound 3 6.20 50 1,982 3.96 blue 204hr Example 2 Compound 6.78 50 2,104 4.21 blue 181 hr 14 Example 3Compound 6.61 50 2,414 4.82 blue 175 hr 34 Example 4 Compound 6.09 502,067 4.13 blue 189 hr 51 Example 5 Compound 6.35 50 2,431 4.86 blue 202hr 24 Example 6 Compound 6.24 50 2,574 5.14 blue 207 hr 26 Example 7Compound 1 5.98 50 2,248 4.50 blue 179 hr Example 8 Compound 6.83 502,399 4.79 blue 196 hr 13 Example 9 Compound 5.79 50 2,117 4.23 blue 172hr 44 Example 10 EML's host 6.46 50 3,080 6.16 blue 223 hr Compound 26,ETL Compound 34 Example 11 EML's host 6.21 50 3,230 6.46 blue 218 hrCompound 26, ETL Compound 51 Example 12 HTL 5.68 50 2,896 5.79 blue 234hr Compound 13 EML's host Compound 26, ETL Compound 3 ComparativeDNA-DPVBi 7.85 50 1,560 3.12 blue 113 hr Example 1

Example 13

To manufacture an anode, a corning 15 Ω/cm² (1200 Å) ITO glass substratewas cut to a size of 50 mm×50 mm×0.7 mm and then sonicated in isopropylalcohol and pure water each for five minutes, and then cleaned byirradiation of ultraviolet rays for 30 minutes and exposure to ozone.The resulting glass substrate was loaded into a vacuum depositiondevice.

Then, 2-TNATA, which is a HIL material, was vacuum-deposited on theglass substrate to form a HIL having a thickness of about 600 Å. Then,4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), which is a holetransporting compound, was vacuum-deposited on the HIL to form a HTLhaving a thickness of about 300 Å.

Then, the Compound 70 as a blue phosphorescent host and a widely knowncompound FIrpic as a blue phosphorescent dopant were simultaneouslydeposited on the HTL in a weight ratio of 90:10 to form an EML having athickness of about 300 Å.

Then, Alq3 was deposited on the EML to form an ETL having a thickness of300 Å, and then LiF, which is a halogenated alkali metal, was depositedon the ETL to form an EIL having a thickness of 10 Å. Then, Al wasvacuum-deposited on the EEL to form a cathode having a thickness of 3000Å, thereby forming an LiF/Al electrode and completing the manufacture ofan organic light-emitting device.

Example 14

An organic light-emitting device was manufactured in the same manner asin Example 13, except that Compound 74 was used, instead of Compound 70,to form the EML.

Example 15

An organic light-emitting device was manufactured in the same manner asin Example 13, except that Compound 82 was used, instead of Compound 70,to form the EML.

Example 16

An organic light-emitting device was manufactured in the same manner asin Example 13, except that Compound 83 was used, instead of Compound 70,to form the EML.

Example 17

An organic light-emitting device was manufactured in the same manner asin Example 13, except that the known host CBP and known dopant FIrpicwere used to form the EML, and Compound 72 was used, instead of theknown Alq3, used to form the ETL on the EML.

Example 18

An organic light-emitting device was manufactured in the same manner asin Example 17, except that Compound 84 was used, instead of Compound 72,to form the ETL.

Example 19

An organic light-emitting device was manufactured in the same manner asin Example 17, except that Compound 92 was used, instead of Compound 72,to form the ETL.

Example 20

An organic light-emitting device was manufactured in the same manner asin Example 13, except that Compound 87 was used, instead of NPB, to formthe HTL, and a widely known host CBP and a widely-known dopant FIrpicwere used to form the EML.

Example 21

An organic light-emitting device was manufactured in the same manner asin Example 13, except that Compound 74 was used as a blue phosphorescenthost to form the EML, and Compound 72 was used to form the ETL.

Example 22

An organic light-emitting device was manufactured in the same manner asin Example 21, except that Compound 92 was used, instead of Compound 72,to form the ETL.

Example 23

An organic light-emitting device was manufactured in the same manner asin Example 13, except that Compound 87 was used, instead of NPB, to formthe HTL, Compound 82 was used as a blue phosphorescent host to form theEML, and Compound 84 was used, instead of Alq3, to form the ETL.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 13, except that a widely known blue phosphorescent host CBPwas used, instead of Compound 70, to form the EML.

Comparative Example 3

An organic light-emitting device was manufactured in the same manner asin Example 22, except that a widely known blue fluorescent dopant DPVBiwas used to form the EML.

When the heterocyclic compounds of Formula 1 wherein X₁ and X₂ are —S—were used as a fluorescent/phosphorescent host or a fluorescent dopantof an EML, an ETL material and/or a HTL material of an organiclight-emitting device, in the phosphorescent organic light-emittingdevices driving voltages were lower by about 1V or greater than theorganic light-emitting device of Comparative Example 2, and good I-V-Lcharacteristics with improved efficiency were attained. The organiclight-emitting devices of Examples 13-16 including the heterocycliccompounds of Formula 1 as phosphorescent hosts are found to have lowerdriving voltages by about 1V, higher efficiencies, and longer lifetimesthan the organic light-emitting device of Comparative Example 2. Theorganic light-emitting devices of Examples 17-19 including theheterocyclic compounds of Formula 1 as ETL materials are found to havehigher efficiencies by about 145% or greater, and longer lifetimes thanthe organic light-emitting device of Comparative Example 2. The organiclight-emitting device of Example 20 including the heterocyclic compoundof Formula 1 as a HTL material is found to have a longer lifetime byabout 185% or greater than the organic light-emitting device ofComparative Example 2. The organic light-emitting devices of Examples 21and 22 including the heterocyclic compounds of Formula 1 as aphosphorescent host or an ETL material are found to have higherefficiencies by about 160% than the organic light-emitting device ofComparative Example 2. The organic light-emitting device of Example 23including the heterocyclic compounds of Formula 1 as a phosphorescenthost of an EML, a HTL material, and an ETL material is found to have alower driving voltage by about 1.1V, a higher efficiency by about 170%,and a longer lifetime by about 180% or greater than the organiclight-emitting device of Comparative Example 2. The characteristics ofthe organic light-emitting devices of Examples 13-23 and ComparativeExamples 2 and 3 are shown in Table 1 below.

TABLE 2 Driving Current Half life-span EML or HTL voltage densityLuminance Efficiency Luminescent (hr @100 material (V) (mA/cm²) (cd/m²)(cd/A) color mA/cm²) Example 13 Phosphorescent 6.79 50 2,288 4.58 blue168 hr host Compound 70 Example 14 Phosphorescent 6.85 50 2,342 4.68blue 176 hr host Compound 74 Example 15 Phosphorescent 6.81 50 2,4784.95 blue 204 hr host Compound 82 Example 16 Phosphorescent 6.70 502,413 4.83 blue 183 hr host Compound 83 Example 17 HTL material 6.76 502,349 4.69 blue 212 hr Compound 72 Example 18 HTL material 6.89 50 2,3724.74 blue 198 hr Compound 84 Example 19 ETL material 6.91 50 2,290 4.58blue 201 hr Compound 92 Example 20 HTL material 6.68 50 2,412 4.82 blue210 hr Compound 87 Example 21 Phosphorescent 6.53 50 2.472 4.94 blue 216hr host Compound 74, ETL material Compound 72 Example 22 Phosphorescent6.81 50 2,602 5.20 blue 227 hr host Compound 74, ETL material Compound92 Example 23 HTL material 6.67 50 2,608 5.21 blue 208 hr Compound 87,Phosphorescent host Compound 82, ETL material Compound 84 ComparativeCBP-Firpic 7.85 50 1,560 3.12 blue 113 hr Example 2 ComparativeCBP-DPVBi 8.12 50 1,432 2.86 blue 121 hr Example 3

As described above, novel heterocyclic compounds according to the one ormore of the above embodiments of the present invention have goodemission characteristics and charge transporting capabilities, and thusmay be used as an electron injecting/transporting material for mostcolor-fluorescent and phosphorescent devices, such as red, green, blue,and white fluorescent and phosphorescent devices, especially as alight-emitting material of green, blue, or white fluorescent device.Thus, an organic light-emitting device with high-efficiency, low-drivingvoltage, high luminance and long lifespan may be manufactured using theheterocyclic compounds.

While the present invention has been particularly shown and describedwith reference to exemplary embodiments thereof, it will be understoodby those of ordinary skill in the art that various changes in form anddetails may be made therein without departing from the spirit and scopeof the present invention as defined by the following claims.

What is claimed is:
 1. A compound represented by Formula 1 below:

wherein, in Formula 1, R₂ to R₄ and R₇ to R₉ are each independently ahydrogen atom, a deuterium atom, a halogen group, a cyano group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₁-C₅₀ alkenyl group, a substituted or unsubstitutedC₅-C₆₀ aryl group, an amino group substituted with a substituted orunsubstituted C₅-C₆₀ aryl group, a substituted or unsubstituted C₃-C₆₀heteroaryl group, or a substituted or unsubstituted C₆-C₆₀ condensedpolycyclic group; R₁, R₅, R₁₀ and R₆ are each independently asubstituted or unsubstituted ethyl group, a propyl group, an isobutylgroup, a sec-butyl group, a pentyl group, an iso-amyl group, a hexylgroup, a heptyl group, an octyl group, a nonanyl group, or a dodecylgroup; X₁ and X₂ are each independently —N(R₂₀)— or —S—; adjacentsubstituents among R₁ to R₅ or those among R₆ to R₁₀ are optionallylinked to form a ring; and R₂₀ is a hydrogen atom, a deuterium atom, ahalogen group, a cyano group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₁-C₅₀ alkenyl group, asubstituted or unsubstituted C₅-C₆₀ aryl group, an amino groupsubstituted with a substituted or unsubstituted C₅-C₆₀ aryl group, asubstituted or unsubstituted C₃-C₆₀ heteroaryl group, or a substitutedor unsubstituted C₆-C₆₀ condensed polycyclic group.
 2. A compound ofclaim 1, wherein, in Formula 1, R₂ to R₄, R₇ to R₉, and R₂₀ are eachindependently a hydrogen atom, a deuterium atom, a halogen group, acyano group, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₁-C₂₀ alkenyl group, a substituted orunsubstituted C₅-C₃₀ aryl group, an amino group substituted with asubstituted or unsubstituted C₅-C₃₀ aryl group, a substituted orunsubstituted C₃-C₃₀ heteroaryl group, or a substituted or unsubstitutedC₆-C₃₀ condensed polycyclic group.
 3. A compound of claim 1, wherein, inFormula 1, R₂ to R₄, R₇ to R₉, and R₂₀ are each independently selectedfrom the group consisting of a hydrogen atom, a deuterium atom, ahalogen atom, a cyano group, a substituted or unsubstituted C₁-C₂₀ alkylgroup, a substituted or unsubstituted C₁-C₂₀ alkenyl group, and groupsrepresented by Formulae 2a to 2j below:

wherein, in Formulae 2a to 2j, Q₁ is represented by —C(R₃₀)(R₃₁)—,—N(R₃₂)—, —N(-*)-, —S—, or —O—; Y₁, Y₂, and Y₃ are each independentlyrepresented by —N═, —N(-*)-, —S—, —O—, —C(R₃₃)=, or —C(-*)=; Z₁, Z₂,Ar₁₂, Ar₁₃, R₃₀, R₃₁, R₃₂, and R₃₃ are each independently selected fromthe group consisting of a lone pair electron, a hydrogen atom, adeuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted C₅-C₂₀aryl group, a substituted or unsubstituted C₃-C₂₀ heteroaryl group, asubstituted or unsubstituted C₆-C₂₀ condensed polycyclic group, a nitrogroup, a hydroxyl group, and a carboxy group; Ar₁₁ is selected from thegroup consisting of a substituted or unsubstituted C₁-C₂₀ alkylenegroup, a substituted or unsubstituted C₅-C₂₀ arylene group, and asubstituted or unsubstituted C₃-C₂₀ heteroarylene group; p is an integerfrom 1 to 10; r is an integer from 0 to 5; and * is a binding site.
 4. Acompound of claim 1, wherein, in Formula 1, R₂ to R₄, R₇ to R₉, and R₂₀are each independently selected from the group consisting of a hydrogenatom, a deuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted C₁-C₂₀alkenyl group, and groups represented by Formulae 3a to 3h below:

wherein, in Formulae 3a to 3h, Y₁ is represented by —N═, —S—, —O—, or—C(R₃₄)=; Z₁ and Z₂ are each independently selected from the groupconsisting of a hydrogen atom, a deuterium atom, a halogen group, acyano group, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₅-C₂₀ aryl group, a substituted orunsubstituted C₃-C₂₀ heteroaryl group, a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group, a nitro group, a hydroxyl group, anda carboxy group; p and q are each independently an integer from 1 to 7;and * is a binding site.
 5. A compound of claim 1, wherein the compoundrepresented by Formula 1 is symmetrical.
 6. A compound of claim 1,wherein, in Formula 1, R₂ to R₄, R₇ to R₉, and R₂₀ are eachindependently selected from the group consisting of a hydrogen atom, adeuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted C₁-C₂₀alkenyl group, and groups represented by Formulae 2a to 2j below; andthe compound represented by Formula 1 is symmetrical:

wherein, in Formulae 2a to 2j, Q₁ is represented by —C(R₃₀)(R₃₁)—,—N(R₃₂)—, —N(-*)-, —S—, or —O—; Y₁, Y₂, and Y₃ are each independentlyrepresented by —N═, —N(-*)-, —S—, —O—, —C(R₃₃)=, or —C(-*)=; Z₁, Z₂,Ar₁₂, Ar₁₃, R₃₀, R₃₁, R₃₂, and R₃₃ are each independently selected fromthe group consisting of a lone pair electron, a hydrogen atom, adeuterium atom, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₅-C₂₀ aryl group, a substituted orunsubstituted C₃-C₂₀ heteroaryl group, a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group, a halogen atom, a cyano group, anitro group, a hydroxyl group, and a carboxy group; Ar₁₁ is selectedfrom the group consisting of a substituted or unsubstituted C₁-C₂₀alkylene group, a substituted or unsubstituted C₅-C₂₀ arylene group, anda substituted or unsubstituted C₃-C₂₀ heteroarylene group; p is aninteger from 1 to 10; r is an integer from 0 to 5; and * is a bindingsite.
 7. A compound of claim 1, wherein the compound of Formula 1 is oneof the compounds below:


8. An organic light-emitting device comprising: a first electrode; asecond electrode; and an organic layer between the first electrode andthe second electrode, wherein the organic layer comprises a first layerincluding a compound represented by Formula 1 below:

wherein, in Formula 1, R₁ to R₁₀ are each independently a hydrogen atom,a deuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₁-C₅₀alkenyl group, a substituted or unsubstituted C₅-C₆₀ aryl group, anamino group substituted with a substituted or unsubstituted C₅-C₆₀ arylgroup, a substituted or unsubstituted C₃-C₆₀ heteroaryl group, or asubstituted or unsubstituted C₆-C₆₀ condensed polycyclic group; X₁ andX₂ are each independently —N(R₂₀)— or —S—; adjacent substituents amongR₁ to R₅ or those among R₆ to R₁₀ are optionally linked to form a ring;and R₂₀ is a hydrogen atom, a deuterium atom, a halogen group, a cyanogroup, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₁-C₅₀ alkenyl group, a substituted or unsubstitutedC₅-C₆₀ aryl group, an amino group substituted with a substituted orunsubstituted C₅-C₆₀ aryl group, a substituted or unsubstituted C₃-C₆₀heteroaryl group, or a substituted or unsubstituted C₆-C₆₀ condensedpolycyclic group.
 9. The organic light-emitting device of claim 8,wherein the first layer comprises at least one layer selected from thegroup consisting of a hole injection layer, a hole transport layer, alayer having both hole injection and hole transport capabilities, anelectron injection layer, an electron transport layer, and a functionallayer having both electron injection and electron transportcapabilities.
 10. The organic light-emitting device of claim 8, whereinthe organic layer is an emission layer comprising a compound ofFormula
 1. 11. The organic light-emitting device of claim 8, wherein theorganic layer comprises an emission layer, a hole transport layer, andan electron transport layer; and the first layer is an emission layerthat further comprises an anthracene compound, an arylamine compound, ora styryl compound.
 12. The organic light-emitting device of claim 8,wherein the organic layer comprises an emission layer, a hole transportlayer, and an electron transport layer; and the first layer is anemission layer which further comprises a phosphorescent compound. 13.The organic light-emitting device of claim 8, wherein the first layer isa blue emission layer.
 14. The organic light-emitting device of claim 8,wherein the first layer is a blue emission layer, and comprises acompound of Formula
 1. 15. The organic light-emitting device of claim 8,wherein the organic layer further comprises a hole injection layer, ahole transport layer, a layer having both hole injection and holetransport capabilities, an emission layer, a hole blocking layer, anelectron transport layer, an electron injection layer, or a combinationof at least two thereof.
 16. The organic light-emitting device of claim15, wherein at least one of the hole injection layer, the hole transportlayer, and the layer having hole injection and hole transportcapabilities further comprises a charge generating material.
 17. Theorganic light-emitting device of claim 15, wherein the electrontransport layer comprises an electron transporting organic material anda metal-containing material.
 18. The organic light-emitting device ofclaim 17, wherein the metal-containing material comprises a lithium (Li)complex.
 19. The organic light-emitting device of claim 8, wherein thefirst layer is formed from the compound of Formula 1 below using a wetprocess:

wherein, in Formula 1, R₁ to R₁₀ are each independently a hydrogen atom,a deuterium atom, a halogen group, a cyano group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₁-C₅₀alkenyl group, a substituted or unsubstituted C₅-C₆₀ aryl group, anamino group substituted with a substituted or unsubstituted C₅-C₆₀ arylgroup, a substituted or unsubstituted C₃-C₆₀ heteroaryl group, or asubstituted or unsubstituted C₆-C₆₀ condensed polycyclic group; X₁ andX₂ are each independently —N(R₂₀)— or —S—; adjacent substituents amongR₁ to R₅ or those among R₆ to R₁₀ are optionally linked to form a ring;and R₂₀ is a hydrogen atom, a deuterium atom, a halogen group, a cyanogroup, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₁-C₅₀ alkenyl group, a substituted or unsubstitutedC₅-C₆₀ aryl group, an amino group substituted with a substituted orunsubstituted C₅-C₆₀ aryl group, a substituted or unsubstituted C₃-C₆₀heteroaryl group, or a substituted or unsubstituted C₆-C₆₀ condensedpolycyclic group.
 20. A flat panel display device comprising the organiclight-emitting device of claim 8, wherein the first electrode of theorganic light-emitting device is electrically connected to a sourceelectrode or a drain electrode of a thin-film transistor.